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101. Photochemical Synthesis and Electronic Properties of Extended Corannulenes with Variable Fluorination Pattern

Author:
Halilovic, Dzeneta; Budanović, Maja; Wong, Zeng R.; Webster, Richard D.; Huh, June; Stuparu, Mihaiela C.
Source:
Journal of organic chemistry 2018 v.83 no.7 pp. 3529-3536
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; fluorine; moieties; organic chemistry; photochemistry; polycyclic aromatic hydrocarbons; spectral analysis; ultraviolet-visible spectroscopy;     Show all 9 Subjects
Abstract:
... The first family of extended and fluorinated corannulenes is prepared through a highly efficient and modular synthetic strategy. In this strategy, corannulene aldehyde could be combined with the fluorine-carrying phosphonium ylides to furnish stilbene-like vinylene precursors. A photochemically induced oxidative cyclization process of these precursors gives rise to the fluorinated and curved polyc ...
DOI:
10.1021/acs.joc.7b03146

102. Silver-Free Palladium-Catalyzed C(sp3)–H Arylation of Saturated Bicyclic Amine Scaffolds

Author:
Coomber, Charlotte E.; Benhamou, Laure; Bučar, Dejan-Krešimir; Smith, Peter D.; Porter, Michael J.; Sheppard, Tom D.
Source:
Journal of organic chemistry 2018 v.83 no.5 pp. 2495-2503
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; arylation; catalytic activity; chemical structure; esters; ketones; organic chemistry; organobromine compounds; organoiodine compounds; palladium; phenols;     Show all 11 Subjects
Abstract:
... Herein, we report a silver-free Pd(II)-catalyzed C(sp³)–H arylation of saturated bicyclic and tricyclic amine scaffolds. The reaction provides good yields using a range of aryl iodides and aryl bromides including functionalized examples bearing aldehydes, ketones, esters, free phenols, and heterocycles. The methodology has been applied to medicinally relevant scaffolds. Two of the intermediate pal ...
DOI:
10.1021/acs.joc.7b02665

103. Origin of Stereocontrol in Photoredox Organocatalysis of Asymmetric α-Functionalizations of Aldehydes

Author:
Li, Man; Sang, Yueqian; Xue, Xiao-Song; Cheng, Jin-Pei
Source:
Journal of organic chemistry 2018 v.83 no.6 pp. 3333-3338
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; catalytic activity; enamines; enantioselectivity; models; moieties; organic chemistry; redox reactions;     Show all 9 Subjects
Abstract:
... The merger of the common photoredox catalyst Ru(bpy)₃Cl₂ with an imidazolidinone organocatalyst by MacMillan et al. has enabled a series of highly enantioselective α-functionalizations of aldehydes, a landmark discovery in photoredox organocatalysis. Herein, we present the theoretical investigation into the origin of enantioselectivity in asymmetric radical additions to the MacMillan imidazolidino ...
DOI:
10.1021/acs.joc.8b00469

104. Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration

Author:
Andreou, Dimitrios; Kallitsakis, Michael G.; Loukopoulos, Edward; Gabriel, Catherine; Kostakis, George E.; Lykakis, Ioannis N.
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 2104-2113
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amines; catalysts; chemical reactions; chemical structure; ketones; nitroalkenes; nitrogen; organic chemistry; protocols; pyrroles; regioselectivity;     Show all 12 Subjects
Abstract:
... The facile copper-catalyzed synthesis of polysubstituted pyrroles from aldehydes, amines, and β-nitroalkenes is reported. Remarkably, the use of α-methyl-substituted aldehydes provides efficient access to a series of tetra- and pentasubstituted pyrroles via an overwhelming 1,2-phenyl/alkyl migration. The present methodology is also accessible to non α-substituted aldehydes, yielding the correspond ...
DOI:
10.1021/acs.joc.7b03051

105. Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol under Neutral Conditions Catalyzed by a Metal–Ligand Bifunctional Catalyst [Cp*Ir(2,2′-bpyO)(H2O)]

Author:
Wang, Rongzhou; Tang, Yawen; Xu, Meng; Meng, Chong; Li, Feng
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 2274-2281
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; chemoselectivity; hydrogenation; isopropyl alcohol; ketones; ligands; moieties; organic chemistry;     Show all 9 Subjects
Abstract:
... A Cp*Ir complex bearing a functional bipyridonate ligand [Cp*Ir(2,2′-bpyO)(H₂O)] was found to be a highly efficient and general catalyst for transfer hydrogenation of aldehydes and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. It was noteworthy that many readily reducible or labile functional groups such as nitro, cyano, ester, and halide ...
DOI:
10.1021/acs.joc.7b03174

106. Aminocatalyzed Synthesis of Enantioenriched Phenalene Skeletons through a Friedel–Crafts/Cyclization Strategy

Author:
Giardinetti, Maxime; Marrot, Jérôme; Greck, Christine; Moreau, Xavier; Coeffard, Vincent
Source:
Journal of organic chemistry 2018 v.83 no.2 pp. 1019-1025
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; 2-naphthol; catalytic activity; chemical reactions; chemical structure; enantioselectivity; fluorescence; organic chemistry; triethylamine;     Show all 9 Subjects
Abstract:
... A series of enantioenriched phenalene-derived compounds were accessed by a Friedel–Crafts/cyclization strategy. Starting from α,β-unsaturated aldehydes and 2-naphthol derivatives, high levels of enantioselectivity were obtained through iminium–enamine catalysis. The catalytic system composed of a diphenylprolinol silyl ether organocatalyst and triethylamine as a base was applied to a combination o ...
DOI:
10.1021/acs.joc.7b02629

107. Nickel-Catalyzed Reductive Etherification of Aldehydes at Room Temperature: C–O vs C–C Bond Formation

Author:
Rahimi, Sajjad; Panahi, Farhad; Bahmani, Marzieh; Iranpoor, Nasser
Source:
Journal of organic chemistry 2018 v.83 no.2 pp. 973-979
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; ambient temperature; benzyl alcohol; chemical bonding; chemical reactions; chemical structure; ethers; ethylene glycol; organic chemistry;     Show all 9 Subjects
Abstract:
... The reaction of secondary and tertiary benzyl alcohols activated by 2,4,6-trichloro-1,3,5-triazine (TCT) with aldehydes in the presence of NiCl₂·dmg as a precatalyst in ethylene glycol afforded ethers at room temperature. A selective C–O vs C–C bond formation was observed for the secondary and tertiary benzyl alcohols in comparison with primary ones. ...
DOI:
10.1021/acs.joc.7b02281

108. Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Author:
Sherwood, Alexander M.; Williamson, Samuel E.; Johnson, Stephanie N.; Yilmaz, Anil; Day, Victor W.; Prisinzano, Thomas E.
Source:
Journal of organic chemistry 2018 v.83 no.2 pp. 980-992
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; epoxides; fungi; macrolides; organic chemistry; protocols; regioselectivity; stereoselective synthesis;     Show all 10 Subjects
Abstract:
... A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (−)-aspinolid ...
DOI:
10.1021/acs.joc.7b02324

109. Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Author:
Ji, Fanghua; Li, Jianxiao; Li, Xianwei; Guo, Wei; Wu, Wanqing; Jiang, Huanfeng
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 104-112
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; catalytic activity; chemical reactions; chemical structure; imines; organic chemistry; phthalimide;     Show all 8 Subjects
Abstract:
... Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H₂O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily a ...
DOI:
10.1021/acs.joc.7b02433

110. Direct Wittig Olefination of Alcohols

Author:
Li, Qiang-Qiang; Shah, Zaher; Qu, Jian-Ping; Kang, Yan-Biao
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 296-302
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; aerobic conditions; air; alkenes; chemical structure; drugs; glycols; organic chemistry; oxidants; polymerization; resveratrol;     Show all 11 Subjects
Abstract:
... A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefinat ...
DOI:
10.1021/acs.joc.7b02720

111. Stereoselective Total Synthesis of Macrophage-Produced Prohealing 14,21-Dihydroxy Docosahexaenoic Acids

Author:
Nishimura, Keita; Sakaguchi, Tsuyoshi; Nanba, Yutaro; Suganuma, Yuta; Morita, Masao; Hong, Song; Lu, Yan; Jun, Bokkyoo; Bazan, Nicolas G.; Arita, Makoto; Kobayashi, Yuichi
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 154-166
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; docosahexaenoic acid; epoxidation reactions; epoxides; moieties; optical isomerism; organic chemistry; stereoisomers; stereoselectivity;     Show all 10 Subjects
Abstract:
... Synthesis of 14S,21R- and 14S,21S-dihydroxy-DHA (diHDHA) among the four possible stereoisomers of 14,21-diHDHA was studied. Methyl (R)-lactate (>97% ee), selected as a C20–C22 fragment (DHA numbering), was converted to the C17–C22 phosphonium salt, which was subjected to a Wittig reaction with racemic C16-aldehyde of the C12–C16 part with the TMS and TBS-oxy groups at C12 and C14, yielding the C12 ...
DOI:
10.1021/acs.joc.7b02510

112. Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones

Author:
Wang, Weifan; Shen, Xingchao; Zhao, Fengyi; Jiang, Huan; Yao, Weiwei; Pullarkat, Sumod A.; Xu, Li; Ma, Mengtao
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 69-74
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; ambient temperature; catalysts; chemical reactions; chemoselectivity; iodides; ketones; moieties; organic chemistry; protocols; ytterbium;     Show all 11 Subjects
Abstract:
... The well-defined heavy rare-earth ytterbium iodide complex 1 (L₂YbI) has been successfully employed as an efficient catalyst for the hydroboration of a wide range of aldehydes and ketones with pinacolborane (HBpin) at room temperature. The protocol requires low catalyst loadings (0.1–0.5 mol %) and proceeds rapidly (>99% conversion in <10 min). Additionally, catalyst 1 shows a good functional grou ...
DOI:
10.1021/acs.joc.7b02076

113. Diverse Chemosensitizing 8,9-Secolindenane-Type Sesquiterpenoid Oligomers and Monomers from Sarcandra glabra

Author:
Chi, Jun; Wei, Shanshan; Gao, Hongliang; Xu, Dingqiao; Zhang, Lina; Yang, Lei; Xu, Wenjun; Luo, Jun; Kong, Lingyi
Source:
Journal of organic chemistry 2019 v.84 no.14 pp. 9117-9126
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Sarcandra glabra; X-ray diffraction; bioassays; biomimetics; chemical bonding; chemical reactions; chemical structure; chemosensitization; circular dichroism spectroscopy; doxorubicin; lactones; leaves; maleic anhydrides; mass spectrometry; multiple drug resistance; nuclear magnetic resonance spectroscopy; nucleoproteins; organic chemistry; phytochemicals; sesquiterpenoids;     Show all 21 Subjects
Abstract:
... The theoretical analysis and biomimetic conversion confirmed that the oxidative cleavage of the Δ⁸,⁹ double bond of chloranthalactone A (I), an abundant lindenane-type sesquiterpenoid in Chloranthaceae plants, generates 8,9-secolindenane (II) with active aldehyde and maleic anhydride fragments that can capture other fragments and produce oligomeric molecules. A careful phytochemical investigation ...
DOI:
10.1021/acs.joc.9b00986

114. Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

Author:
Kumar, Sonu; Cruz-Hernández, Carlos; Pal, Shilpi; Saunthwal, Rakesh K.; Patel, Monika; Tiwari, Rakesh K.; Juaristi, Eusebio; Verma, Akhilesh K.
Source:
Journal of organic chemistry 2015 v.80 no.21 pp. 10548-10560
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; organic chemistry; regioselectivity;     Show all 3 Subjects
Abstract:
... An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a–t and benzofuropyridines 8a–p by the reaction of o-alkynyl aldehyde 4a–t and 5a–p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excell ...
DOI:
10.1021/acs.joc.5b01647

115. Base-Mediated Three-Component Tandem Reactions for the Synthesis of Multisubstituted Pyrimidines

Author:
Liu, Dongqing; Guo, Wei; Wu, Wanqing; Jiang, Huanfeng
Source:
Journal of organic chemistry 2017 v.82 no.24 pp. 13609-13616
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkynes; amidines; chemical reactions; chemical structure; organic chemistry; pyrimidines;     Show all 7 Subjects
Abstract:
... A base-mediated three-component tandem reaction for the synthesis of multisubstituted pyrimidines from amidines, aryl alkynes, and aldehydes in a one-pot manner has been developed. Advantages of this transformation include being transition-metal-free, high efficiency, available starting materials, and being environmentally friendly. ...
DOI:
10.1021/acs.joc.7b02113

116. Synthesis of [1,3,4]Thiadiazolo[3′,2′:1,2]imidazo[4,5-c]quinolines including Pictet–Spengler Reaction and Exploration of Their C-2 Reactivity through SNAr

Author:
Place, Matthieu; Copin, Chloé; Apotrosoaei, Maria; Constantin, Sandra; Vasincu, Ioana Mirela; Profire, Lenuta; Buron, Frédéric; Routier, Sylvain
Source:
Journal of organic chemistry 2017 v.82 no.24 pp. 13700-13707
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; chemical structure; hydrides; organic chemistry; oxidation; quinolines;     Show all 7 Subjects
Abstract:
... This work reports the design of [1,3,4]thiadiazolo[3′,2′:1,2]imidazo[4,5-c]quinolines using a Pictet–Spengler reaction. The scope of the reaction was achieved from 6-(2-aminophenyl)imidazo[2,1-b][1,3,4]thiadiazole derivatives and available aldehydes. A wide range of aldehydes were employed to examine the scope of the cyclization. In parallel, a mechanism investigation was realized and showed a hyd ...
DOI:
10.1021/acs.joc.7b02565

117. Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment

Author:
Li, Yifei; Jackson, Kelvin E.; Charlton, Andrew; Le Neve-Foster, Ben; Khurshid, Asma; Rudy, Heinrich-K. A.; Thompson, Amber L.; Paton, Robert S.; Hodgson, David. M.
Source:
Journal of organic chemistry 2017 v.82 no.19 pp. 10479-10488
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical structure; enamines; enantioselectivity; ethylation; organic chemistry;     Show all 6 Subjects
Abstract:
... Quantum chemical studies of C-ethylation of 1-methyl- and 1,4,4-trimethyl-tropane-derived enamines predict good (89:11 er, B3LYP) and high (98:2 er, B3LYP) levels, respectively, of asymmetric induction in the resulting α-alkylated aldehydes. The nonracemic tropanes were synthesized using Mannich cyclization strategies (Robinson-Schöpf and by way of a Davis-type N-sulfinyl amino bisketal, respecti ...
DOI:
10.1021/acs.joc.7b01954

118. Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

Author:
Vishwanatha, Thimmalapura M.; Kurpiewska, Katarzyna; Kalinowska-Tłuścik, Justyna; Dömling, Alexander
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9585-9594
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; bioactive compounds; chemical reactions; cysteine; enantiomers; organic chemistry; thiazoles;     Show all 7 Subjects
Abstract:
... An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing pep ...
DOI:
10.1021/acs.joc.7b01615
PubMed:
28817272
PubMed Central:
PMC5603900

119. Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

Author:
Eshon, Josephine; Landis, Clark R.; Schomaker, Jennifer M.
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9270-9278
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; chemical structure; hydrogenation; isomerization; ligands; organic chemistry; regioselectivity;     Show all 8 Subjects
Abstract:
... The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions minimize competing isomerization and hydrogenation to produce β,γ-unsaturated aldehydes and their derivatives in excellent yields. ...
DOI:
10.1021/acs.joc.7b01140

120. Radical 1,2-Alkylarylation/Acylarylation of Allylic Alcohols with Aldehydes via Neophyl Rearrangement

Author:
Pan, Changduo; Ni, Qingting; Fu, Yu; Yu, Jin-Tao
Source:
Journal of organic chemistry 2017 v.82 no.14 pp. 7683-7688
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; chemical reactions; chemical structure; organic chemistry;     Show all 5 Subjects
Abstract:
... A metal-free 1,2-alkylarylation of allylic alcohols with aliphatic aldehydes through concomitant radical neophyl rearrangement was developed, providing 1,2-diphenyl-3-alkyl propanones in moderate to good yields. Moreover, when cyclopropanecarbaldehyde and aryl carbaldehydes were concerned, acylarylation was involved leading to 1,4-dicarbonyl compounds. ...
DOI:
10.1021/acs.joc.7b01255

121. Asymmetric Synthesis of the Tetraponerine Alkaloids

Author:
Davies, Stephen G.; Fletcher, Ai M.; Houlsby, Ian T. T.; Roberts, Paul M.; Thomson, James E.
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6689-6702
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetates; alkaloids; diamines; diastereoselectivity; hydrogenation; lithium; moieties; organic chemistry;     Show all 9 Subjects
Abstract:
... The asymmetric syntheses of all eight tetraponerine alkaloids (T1–T8) were achieved using the diastereoselective conjugate additions of lithium amide reagents in the key stereodefining steps. Conjugate addition of either lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amide to tert-butyl sorbate was followed by ring-closing metathesis of the resultant ...
DOI:
10.1021/acs.joc.7b00837

122. One-Pot Consecutive Sulfonamidation/ipso-Cyclization Strategy for the Construction of Azaspirocyclohexadienones

Author:
Raji Reddy, Chada; Ranjan, Ravi; Prajapti, Santosh Kumar; Warudikar, Kamalkishor
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6932-6939
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkynes; carbonates; chemical reactions; moieties; organic chemistry;     Show all 6 Subjects
Abstract:
... Harnessing of Morita–Baylis–Hillman (MBH) carbonates of acetylenic aldehydes as handy synthons has allowed a facile synthesis of azaspirocyclohexadienones by sequential DABCO-promoted sulfonamidation/ICl-mediated ipso-iodocyclization reactions. A variety of MBH-carbonates having aryl or heteroaryl groups on the alkyne functionality fruitfully participated in the one-pot ipso-annulation reaction to ...
DOI:
10.1021/acs.joc.7b01285

123. Organocatalytic Direct N-Acylation of Amides with Aldehydes under Oxidative Conditions

Author:
Zheng, Chenguang; Liu, Xiang; Ma, Cheng
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6940-6945
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amides; chemical reactions; chemical structure; organic chemistry; oxidants;     Show all 6 Subjects
Abstract:
... The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in g ...
DOI:
10.1021/acs.joc.7b00457

124. Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of l-α-Amino Aldehydes

Author:
Zamani, Farzad; Pyne, Stephen G.; Hyland, Christopher J. T.
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6819-6830
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; chemical reactions; diastereomers; diastereoselectivity; organic chemistry; oxazolidinones; regioselectivity;     Show all 8 Subjects
Abstract:
... The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected l-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecting groups. A range of 1-allenyl-2-amino alcohols were obtained with excellent regioselectivity and converted to oxazolidinones and dihydrofurans. ...
DOI:
10.1021/acs.joc.7b00969

125. Theoretical Study of the BF3-Promoted Rearrangement of Oxiranyl N-Methyliminodiacetic Acid Boronates

Author:
Vallejos, Margarita M.; Pellegrinet, Silvina C.
Source:
Journal of organic chemistry 2017 v.82 no.11 pp. 5917-5925
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; boron; chemical reactions; energy; hydrogen; methodology; moieties; organic chemistry;     Show all 8 Subjects
Abstract:
... The mechanism of the rearrangement of oxiranyl N-methyliminodiacetyl (MIDA) boronates in dicholoromethane has been extensively investigated with density functional theory. Several reaction pathways were examined. Our results revealed that the most-favorable mechanisms for the BF₃-promoted rearrangement of 2-phenyl oxiranyl MIDA boronate (1) and 1-phenyl oxiranyl MIDA boronate (24) comprise two ste ...
DOI:
10.1021/acs.joc.7b01096

126. Development of a One-Pot Synthetic Method for Multifunctional Oxazole Derivatives Using Isocyanide Dichloride

Author:
Soeta, Takahiro; Matsumoto, Akihiro; Sakata, Yoko; Ukaji, Yutaka
Source:
Journal of organic chemistry 2017 v.82 no.9 pp. 4930-4935
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; chemical reactions; chemical structure; organic chemistry; oxazoles;     Show all 6 Subjects
Abstract:
... A one-pot synthetic method was developed for multifunctional dihydrooxazole and oxazole derivatives. New reaction sequences were developed involving the formation of isocyanide dichloride, an aldol-type reaction with aldehydes, and a nucleophilic addition–elimination reaction, which efficiently afforded the dihydrooxazole and oxazole scaffolds. ...
DOI:
10.1021/acs.joc.7b00296

127. Nickel-Catalyzed Decarbonylation of Aromatic Aldehydes

Author:
Ding, Keying; Xu, Shi; Alotaibi, Rajeh; Paudel, Keshav; Reinheimer, Eric W.; Weatherly, Jessie
Source:
Journal of organic chemistry 2017 v.82 no.9 pp. 4924-4929
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; esters; organic chemistry;     Show all 5 Subjects
Abstract:
... We report here the first systematic study of nickel-catalyzed decarbonylation of aromatic aldehydes under relatively mild conditions. Aldehydes with electron donating groups at para and ortho positions are generally successful with our method. For aldehydes with electron-withdrawing groups, significantly higher yields were achieved for ortho-substituted substrates than para ones, probably due to t ...
DOI:
10.1021/acs.joc.7b00284

128. Squaramide–Sulfonamide Organocatalyst for Asymmetric Direct Vinylogous Aldol Reactions

Author:
Sakai, Takaaki; Hirashima, Shin-ichi; Yamashita, Yoshifumi; Arai, Ryoga; Nakashima, Kosuke; Yoshida, Akihiro; Koseki, Yuji; Miura, Tsuyoshi
Source:
Journal of organic chemistry 2017 v.82 no.9 pp. 4661-4667
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; organic chemistry; stereoselectivity;     Show all 5 Subjects
Abstract:
... Asymmetric direct vinylogous aldol reactions of furan-2(5H)-one with aldehydes in the presence of a catalytic amount of novel squaramide–sulfonamide organocatalyst resulted in the corresponding addition products with high to excellent enantioselectivities. This is the first successful report illustrating an example of highly stereoselective reactions using a squaramide–sulfonamide organocatalyst. ...
DOI:
10.1021/acs.joc.7b00287

129. Assembly of Indolenines, 3-Amino Oxindoles, and Aldehydes into Indolenine-Substituted Spiro[pyrrolidin-2,3′-oxindoles] via 1,3-Dipolar Cycloaddition with Divergent Diastereoselectivities

Author:
Zhu, Guodong; Liu, Siyuan; Wu, Shiqi; Peng, Lianghong; Qu, Jingping; Wang, Baomin
Source:
Journal of organic chemistry 2017 v.82 no.8 pp. 4317-4327
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; diastereoselectivity; organic chemistry;     Show all 5 Subjects
Abstract:
... A novel one-pot 1,3-dipolar cycloaddition of indolenines, 3-aminooxindoles, and aldehydes is reported. The reaction provides indolenine-substituted spiro[pyrrolidin-2,3′-oxindoles] containing four contiguous stereogenic centers in high yields (up to 99%) and excellent diastereoselectivities (up to >20:1 dr) under mild conditions. Remarkably, the inversion of diastereoselectivity could be readily a ...
DOI:
10.1021/acs.joc.7b00316

130. Catalyst-Free Synthesis of Pyrrolo[1,2-a]quinolines via Dehydration/[3 + 2] Cycloaddition Directly from 2-Methylquinolines, Aldehydes, and Alkynoates

Author:
Wu, Fu-song; Zhao, Hai-yuan; Xu, Yan-li; Hu, Kun; Pan, Ying-ming; Ma, Xian-li
Source:
Journal of organic chemistry 2017 v.82 no.8 pp. 4289-4296
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; air; byproducts; chemical reactions; chemical structure; organic chemistry; quinoline;     Show all 7 Subjects
Abstract:
... A simple and efficient catalyst-free synthesis of pyrrolo[1,2-a]quinoline derivatives from 2-methylquinolines, aldehydes, and alkynoates via dehydration/[3 + 2] cycloaddition has been developed. The reaction conditions are tolerant to air, and H₂O is the only byproduct of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic syn ...
DOI:
10.1021/acs.joc.7b00280

131. I2-Mediated Intramolecular C–H Amidation for the Synthesis of N-Substituted Benzimidazoles

Author:
Hu, Zhiyuan; Zhao, Ting; Wang, Manman; Wu, Jie; Yu, Wenquan; Chang, Junbiao
Source:
Journal of organic chemistry 2017 v.82 no.6 pp. 3152-3158
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; benzimidazole; chemical structure; cyclization reactions; imines; iodine; organic chemistry;     Show all 7 Subjects
Abstract:
... A practical intramolecular C–H amidation methodology has been developed using molecular iodine under basic conditions. The required imine substrates were readily obtained by condensation of simple o-phenylenediamine derivatives and aldehydes. The transition-metal-free cyclization reaction described here works well with crude imines and allows for the sequential synthesis of N-protected benzimidazo ...
DOI:
10.1021/acs.joc.7b00142

132. Allylmagnesium Halides Do Not React Chemoselectively Because Reaction Rates Approach the Diffusion Limit

Author:
Read, Jacquelyne A.; Woerpel, K. A.
Source:
Journal of organic chemistry 2017 v.82 no.4 pp. 2300-2305
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; carbonyl compounds; chemical reactions; esters; halides; moieties; organic chemistry;     Show all 7 Subjects
Abstract:
... Competition experiments demonstrate that additions of allylmagnesium halides to carbonyl compounds, unlike additions of other organomagnesium reagents, occur at rates approaching the diffusion rate limit. Whereas alkylmagnesium and alkyllithium reagents could differentiate between electronically or sterically different carbonyl compounds, allylmagnesium reagents reacted with most carbonyl compound ...
DOI:
10.1021/acs.joc.7b00053

133. Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones

Author:
Hazlitt, Robert A.; Tran, Que-Lynn; Sowaileh, Munia F.; Colby, David A.
Source:
Journal of organic chemistry 2017 v.82 no.4 pp. 2231-2236
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amides; chemical structure; ketones; magnesium; organic chemistry; oxidation; synthesis;     Show all 8 Subjects
Abstract:
... 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones are valuable precursors to difluoroenolates following fragmentation during the release of trifluoroacetate; however, there are few synthetic strategies to prepare this unique class of compound. We addressed this issue and report a mild, two-step synthesis of 2,2,4,4,4-pentafluoro-3,3-dihydroxyketones from aldehydes. Specifically, aldehydes are treated wit ...
DOI:
10.1021/acs.joc.6b02863

134. Synthesis of Rings DEF of Solanoeclepin A

Author:
Chuang, Hsiang-Yu; Isobe, Minoru
Source:
Journal of organic chemistry 2017 v.82 no.4 pp. 2045-2058
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical bonding; cleavage (chemistry); cyclization reactions; moieties; organic chemistry;     Show all 6 Subjects
Abstract:
... An improved synthesis of rings DEF of solanoeclepin A has been achieved from ent-Hajos Parrish ketone. A key tricyclo[5.3.2.0¹,⁶]decene intermediate having an additional vinyl group as a precursor of a hydroxyl functionality was synthesized, in which the key steps included (i) a [2,3]-Wittig rearrangement to provide trans-hydroindene with C11(R)-configuration, (ii) the introduction of a vinyl grou ...
DOI:
10.1021/acs.joc.6b02886

135. Stereochemically Defined Various Multisubstituted Alkenes Bearing a Tetrafluoroethylene (−CF2CF2−) Fragment

Author:
Sakaguchi, Yukiho; Yamada, Shigeyuki; Konno, Tsutomu; Agou, Tomohiro; Kubota, Toshio
Source:
Journal of organic chemistry 2017 v.82 no.3 pp. 1618-1631
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Suzuki reaction; alkenes; chemical structure; organic chemistry; stereochemistry; stereoselectivity;     Show all 7 Subjects
Abstract:
... Highly regio- and stereoselective transformation of commercially available 4-bromo-3,3,4,4-tetrafluoro-1-butene into multisubstituted alkenes having a tetrafluoroethylene fragment through Heck reactions and/or Suzuki–Miyaura cross-coupling reactions was established. Thus, the obtained alkenes underwent a smooth reductive coupling reaction with aldehydes under the influence of MeLi/LiBr-free, affor ...
DOI:
10.1021/acs.joc.6b02793

136. Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene

Author:
Zhang, Huaiyuan; Huang, Danfeng; Wang, Ke-Hu; Li, Jun; Su, Yingpeng; Hu, Yulai
Source:
Journal of organic chemistry 2017 v.82 no.3 pp. 1600-1609
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; cyanides; organic chemistry;     Show all 5 Subjects
Abstract:
... A novel and efficient PhI(OAc)₂-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF₃·Et₂O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials. ...
DOI:
10.1021/acs.joc.6b02781

137. Burgess Reagent Facilitated Alcohol Oxidations in DMSO

Author:
Sultane, Prakash R.; Bielawski, Christopher W.
Source:
Journal of organic chemistry 2017 v.82 no.2 pp. 1046-1052
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; chemical structure; dimethyl sulfoxide; ketones; organic chemistry; oxidation;     Show all 7 Subjects
Abstract:
... The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild condition ...
DOI:
10.1021/acs.joc.6b02629

138. Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1H-pyrroles

Author:
Reddy, Chada Raji; Panda, Sujatarani A.; Ramaraju, Andhavaram
Source:
Journal of organic chemistry 2017 v.82 no.2 pp. 944-949
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetates; azides; chemical reactions; moieties; organic chemistry; pyrroles;     Show all 7 Subjects
Abstract:
... A method for the construction of pyrroles bearing a 2-keto or formyl group through the intramolecular oxidative aza-annulation of enynyl azides is reported for the first time. It involves a sequential carbon–nitrogen/carbon–oxygen bond formations, and the combination of AuCl₃ with AgSbF₆ was identified as a suitable reagent system to promote the present reaction. The required enynyl azides are rea ...
DOI:
10.1021/acs.joc.6b02468

139. Intramolecular Acylation of Unactivated Pyridines or Arenes via Multiple C–H Functionalizations: Synthesis of All Four Azafluorenones and Fluorenones

Author:
Laha, Joydev K.; Jethava, Krupal P.; Patel, Sagarkumar; Patel, Ketul V.
Source:
Journal of organic chemistry 2017 v.82 no.1 pp. 76-85
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acylation; chemical structure; fluorenes; nitrogen; organic chemistry; pyridines;     Show all 7 Subjects
Abstract:
... An unprecedented intramolecular acylation of unactivated pyridines via multiple C(sp³/sp²)–H functionalizations of a methyl, hydroxymethyl, or aldehyde group has been developed providing a general access to all four azafluorenones. The application of this protocol is further demonstrated to the synthesis of azafluorenone related fused nitrogen heterocycles and fluorenones. In addition, design and ...
DOI:
10.1021/acs.joc.6b02065

140. One-Pot Synthesis of Diverse Collections of Benzoxazepine and Indolopyrazine Fused to Heterocyclic Systems

Author:
Srinivasulu, Vunnam; Shehadeh, Ihsan; Khanfar, Monther A.; Malik, Omar G.; Tarazi, Hamadeh; Abu-Yousef, Imad A.; Sebastian, Anusha; Baniowda, Nabil; O’Connor, Matthew John; Al-Tel, Taleb H.
Source:
Journal of organic chemistry 2018 v.84 no.2 pp. 934-948
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetonitrile; bioactive properties; chemical structure; drug design; drugs; ethanol; organic chemistry; oxidation; pyrazines; scandium; sodium metabisulfite; synthesis;     Show all 13 Subjects
Abstract:
... The development of efficient and modular synthetic methods for the synthesis of diverse collection of privileged substructures needed for a drug design and discovery campaign is highly desirable. Benzoxazepine and indolopyrazine ring systems form the core structures of distinct members of biologically significant molecules. Several members of these families have gained attention due to their broad ...
DOI:
10.1021/acs.joc.8b02878

141. One-Pot Approach for the Synthesis of Bis-indole-1,4-disubstituted-1,2,3-triazoles

Author:
Saehlim, Natthiya; Kasemsuk, Teerapich; Sirion, Uthaiwan; Saeeng, Rungnapha
Source:
Journal of organic chemistry 2018 v.83 no.21 pp. 13233-13242
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkylation; alkynes; ambient temperature; azides; chemical structure; copper; cycloaddition reactions; iodine; organic chemistry; organobromine compounds; silica; triazoles;     Show all 13 Subjects
Abstract:
... A new strategy for the synthesis of bis-indoletriazoles was developed using a sequential one-pot four-step procedure via I₂ and H₂SO₄–SiO₂ catalyzed Friedel–Crafts reactions of indole with aldehyde followed by N-alkylation with propargyl bromide, azidation, and copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). The reaction proceeded smoothly at room temperature in a short time, and a series ...
DOI:
10.1021/acs.joc.8b02056

142. One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

Author:
Xu, Peng-Wei; Chen, Chen; Liu, Jia-Kuan; Song, Yu-Ting; Zhou, Feng; Yan, Jun; Zhou, Jian
Source:
Journal of organic chemistry 2018 v.83 no.20 pp. 12763-12774
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical structure; cycloaddition reactions; cytotoxicity; diastereoselectivity; enantioselectivity; hydroxylamine; neoplasm cells; organic chemistry; prostatic neoplasms; transcription factor NF-kappa B;     Show all 11 Subjects
Abstract:
... A Sc(OTf)₃-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxindole-tetrahydro-1,2-oxazines with sufficient structural diversity. The corresponding catalytic enantioselective one-pot protocol of aldehydes is also reporte ...
DOI:
10.1021/acs.joc.8b02208

143. Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

Author:
Xi, Zi-Wei; Yang, Lei; Wang, Dan-Yan; Pu, Chao-Dan; Shen, Yong-Miao; Wu, Chuan-De; Peng, Xiao-Gang
Source:
Journal of organic chemistry 2018 v.83 no.19 pp. 11886-11895
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; ambient temperature; amines; catalysts; chemical structure; electron transfer; hydrogen; hydrogenation; imines; organic chemistry; photocatalysis; quantum dots;     Show all 12 Subjects
Abstract:
... CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radi ...
DOI:
10.1021/acs.joc.8b01651

144. α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation

Author:
Eshon, Josephine; Foarta, Floriana; Landis, Clark R.; Schomaker, Jennifer M.
Source:
Journal of organic chemistry 2018 v.83 no.17 pp. 10207-10220
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acrylates; alkenes; carbon monoxide; catalysts; chemical structure; diastereoselectivity; electronics; hydrogenation; ligands; nuclear magnetic resonance spectroscopy; organic chemistry; regioselectivity; rhodium;     Show all 14 Subjects
Abstract:
... Hydroformylation utilizes dihydrogen, carbon monoxide, and a catalyst to transform alkenes into aldehydes. This work applies chiral bisdiazaphospholane (BDP)- and bisphospholanoethane-ligated rhodium complexes to the hydroformylation of a variety of alkenes to produce chiral tetrasubstituted aldehydes. 1,1′-Disubstituted acrylates bearing electron-withdrawing substituents undergo hydroformylation ...
DOI:
10.1021/acs.joc.8b01431

145. Directed Cu(I)-Catalyzed Carbomagnesiation of 1-Arylcycloprop-2-ene-1-carboxamides En Route to Densely Substituted Functionalized Cyclopropanes

Author:
Edwards, Andrew; Rubin, Michael
Source:
Journal of organic chemistry 2018 v.83 no.15 pp. 8426-8448
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Grignard reagents; Lewis acids; amides; chemical bonding; chemical reactions; chemical structure; copper; diastereoselectivity; organic chemistry; regioselectivity;     Show all 11 Subjects
Abstract:
... Copper-catalyzed, directed addition of Grignard reagents across the strained C═C bond of cyclopropene-3-carboxamides was developed. It was demonstrated that the amide functionality serves as an ultimate directing group allowing for highly efficient control of diastereoselectivity of addition including stereoselectivity of electrophilic trapping with prochiral aldehydes. Also, regioselectivity of c ...
DOI:
10.1021/acs.joc.8b01063

146. Dinuclear Tricyclic Transition State Model for Carbonyl Addition of Organotitanium Reagents: DFT Study on the Activity and Enantioselectivity of BINOLate Titanium Catalysts

Author:
Harada, Toshiro
Source:
Journal of organic chemistry 2018 v.83 no.15 pp. 7825-7835
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; catalysts; chemical reactions; chemical structure; enantioselectivity; ketones; ligands; models; organic chemistry; organometallic compounds; titanium;     Show all 12 Subjects
Abstract:
... In the presence of a catalytic amount of chiral BINOL derivatives (or BINOLs), a mixture of various organometallic compounds with Ti(OⁱPr)₄ undergoes enantioselective addition to aldehydes and ketones. Although the catalyst and reacting nucleophile of the reaction have been elucidated to be (BINOLate)Ti₂(OⁱPr)₆ and RTi(OⁱPr)₃, respectively, little is known about the properties of short-lived inter ...
DOI:
10.1021/acs.joc.8b00712

147. Rhodium(III)-Catalyzed Redox-Neutral Synthesis of Isoquinolinium Salts via C–H Activation of Imines

Author:
Tian, Miaomiao; Zheng, Guangfan; Fan, Xuesen; Li, Xingwei
Source:
Journal of organic chemistry 2018 v.83 no.12 pp. 6477-6488
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; aromatic hydrocarbons; carbon-hydrogen bond activation; chemical reactions; chemical structure; diazo compounds; imines; organic chemistry; rhodium; salts; zinc;     Show all 11 Subjects
Abstract:
... Redox-neutral synthesis of isoquinolinium salts via C–H activation of presynthesized or in situ formed imines and coupling with α-diazo ketoesters has been realized, where a zinc salt promotes cyclization as well as provides a counteranion. Under three-component conditions, both ketone and aldehydes are viable arene sources. The coupling of imines with diazo malonates under similar conditions affo ...
DOI:
10.1021/acs.joc.8b00758

148. Directed C–H Bond Oxidation of (+)-Pleuromutilin

Author:
Ma, Xiaoshen; Kucera, Roman; Goethe, Olivia F.; Murphy, Stephen K.; Herzon, Seth B.
Source:
Journal of organic chemistry 2018 v.83 no.13 pp. 6843-6892
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; antibiotics; carboxylic acids; chemical bonding; diterpenoids; farmed animal species; metabolites; moieties; organic chemistry; oxidation; silylation; structure-activity relationships; synthesis;     Show all 13 Subjects
Abstract:
... Antibiotics derived from the diterpene fungal metabolite (+)-pleuromutilin (1) are useful agents for the treatment Gram-positive infections in humans and farm animals. Pleuromutilins elicit slow rates of resistance development and minimal cross-resistance with existing antibiotics. Despite efforts aimed at producing new derivatives by semisynthesis, modification of the tricyclic core is underexplo ...
DOI:
10.1021/acs.joc.8b00462

149. Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes

Author:
Xiao, Peihong; Tang, Zhixing; Wang, Kai; Chen, Hua; Guo, Qianyou; Chu, Yang; Gao, Lu; Song, Zhenlei
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 1687-1700
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amides; carbon-hydrogen bond activation; chemical bonding; chemoselectivity; hydrolysis; imidoesters; moieties; nuclear magnetic resonance spectroscopy; organic chemistry;     Show all 10 Subjects
Abstract:
... A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)₃ [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combi ...
DOI:
10.1021/acs.joc.7b02868

150. Enantioselective Dearomatization of Alkylpyridiniums by N-Heterocyclic Carbene-Catalyzed Nucleophilic Acylation

Author:
Di Carmine, Graziano; Ragno, Daniele; Bortolini, Olga; Giovannini, Pier Paolo; Mazzanti, Andrea; Massi, Alessandro; Fogagnolo, Marco
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 2050-2057
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; acylation; chemical structure; circular dichroism spectroscopy; enantioselectivity; heterocyclic nitrogen compounds; organic chemistry; regioselectivity; salts;     Show all 10 Subjects
Abstract:
... A chiral NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and enantioselectivities in the range 52–78% ee. The (4R)-absolute configuration of the synthesized compounds has been determined by the TD-DFT simulation of the electronic circular ...
DOI:
10.1021/acs.joc.7b02996

151. Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Author:
Pramanik, Suman; Rej, Supriya; Kando, Shun; Tsurugi, Hayato; Mashima, Kazushi
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 2409-2417
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; carbonyl compounds; chemical reactions; chemical structure; halides; organic chemistry; organic halogen compounds; pyrazines; silyl enol ethers; stereoselective synthesis; stereoselectivity;     Show all 11 Subjects
Abstract:
... Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the ...
DOI:
10.1021/acs.joc.7b03005

152. Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities

Author:
Kawaai, Kazuki; Yamaguchi, Tomoaki; Yamaguchi, Eiji; Endo, Satoshi; Tada, Norihiro; Ikari, Akira; Itoh, Akichika
Source:
Journal of organic chemistry 2018 v.83 no.4 pp. 1988-1996
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; cell proliferation; chemical structure; coumarin; cyclization reactions; free radicals; hydrogen; organic chemistry; photocatalysis; prostate-specific antigen; secretion;     Show all 12 Subjects
Abstract:
... A novel photocatalysis to construct the 3-acyl-4-arylcoumarin framework from simple aldehyde with ynoate is described. The reaction proceeded through an acyl radical intermediate generated by hydrogen atom abstraction from aldehyde, followed by reaction with ynoate and then cyclization to afford coumarins. This valuable radical cyclization reaction gave over 20 coumarin derivatives in moderate to ...
DOI:
10.1021/acs.joc.7b02933

153. Origins of Stereoselectivity in Mannich Reactions Catalyzed by Chiral Vicinal Diamines

Author:
Chen, Shuming; Houk, K. N.
Source:
Journal of organic chemistry 2018 v.83 no.6 pp. 3171-3176
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; ammonium; chemical reactions; chemical structure; density functional theory; diamines; diastereoselectivity; hydrocarbons; hydrogen bonding; ketimines; organic chemistry;     Show all 11 Subjects
Abstract:
... The origins of the enantio- and diastereoselectivities in the Mannich reactions between aldehydes and ketimines catalyzed by chiral vicinal diamines have been determined by density functional theory calculations and distortion–interaction analysis. Computational results indicate a strong energetic preference for hydrogen-bonded nine-membered cyclic transition states. The favored transition states ...
DOI:
10.1021/acs.joc.8b00037

154. Stereocontrol through Synergistic Catalysis in the Enantioselective α-Alkenylation of Aldehyde: A Computational Study

Author:
Patil, Mahendra
Source:
Journal of organic chemistry 2018 v.83 no.3 pp. 1304-1311
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; catalytic activity; chemical reactions; chemical structure; copper; density functional theory; enamines; enantioselectivity; models; organic chemistry; synergism;     Show all 12 Subjects
Abstract:
... We describe the computational study of an interesting class of reactions involving synergistic action of chiral amine and Cu catalyst. The stereoselectivity-determining step of the enantioselective α-alkenylation of aldehyde has been investigated using the density functional theory methods to gain insight into the origin of the product selectivity. We found that the catalytic activation of reactan ...
DOI:
10.1021/acs.joc.7b02822

155. Stereoselectivity of Proline/Cyclobutane Amino Acid-Containing Peptide Organocatalysts for Asymmetric Aldol Additions: A Rationale

Author:
Illa, Ona; Porcar-Tost, Oriol; Robledillo, Carme; Elvira, Carlos; Nolis, Pau; Reiser, Oliver; Branchadell, Vicenç; Ortuño, Rosa M.
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 350-363
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; catalysts; chemical structure; enantioselectivity; methanol; nuclear magnetic resonance spectroscopy; optical isomerism; organic chemistry; peptides; proline; solvents;     Show all 12 Subjects
Abstract:
... Several α,β,α- or α,γ,α-tripeptides, consisting of a central cyclobutane β- or γ-amino acid being flanked by two d- or l-proline residues, have been synthesized and tested as organocatalysts in asymmetric aldol additions. High yields and enantioselectivities have been achieved with α,γ,α-tripeptides, being superior to peptides containing a cyclobutane β-amino acid residue. This is probably due to ...
DOI:
10.1021/acs.joc.7b02745

156. Metal-Free Cascade Oxidative Decarbonylative Alkylation/Arylation of Alkynoates with Alphatic Aldehydes

Author:
Pan, Changduo; Chen, Yu; Song, Shuai; Li, Lei; Yu, Jin-Tao
Source:
Journal of organic chemistry 2016 v.81 no.23 pp. 12065-12069
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkenes; alkylation; arylation; decarboxylation; organic chemistry;     Show all 6 Subjects
Abstract:
... The oxidative difunctionalization of aryl alkynoates with alphatic aldehydes as a cheap and abundant alkyl radical source was developed, providing a variety of trisubstituted alkenes in moderate to good yields. In this reaction, radical decarbonylative alkylation of C-C triple bond, 1,4-aryl migration, and decarboxylation were involved under metal-free conditions. ...
DOI:
10.1021/acs.joc.6b02451

157. Synthesis of Tetrahydro-1H-indeno[1,2-b]pyridine via Cascade Cyclization and Friedel–Crafts Reaction

Author:
Borthakur, Upasana; Borah, Madhurjya; Deka, Manash J.; Saikia, Anil K.
Source:
Journal of organic chemistry 2016 v.81 no.19 pp. 8736-8743
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; antidepressants; cyclization reactions; organic chemistry; pyridines;     Show all 5 Subjects
Abstract:
... A convenient protocol has been established for the synthesis of 1-tosyl-2,3,4,5-tetrahydro-1H-indeno[1,2-b]pyridine via cascade cyclization and Friedel–Crafts reaction of 4-methyl-N-(pent-4-yn-1-yl)benzenesulfonamides and aldehydes in good yields. The methodology has been used for the total synthesis of the antidepressant agent (±)-5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine. ...
DOI:
10.1021/acs.joc.6b00988

158. DABO Boronate Promoted Conjugate Allylation of α,β-Unsaturated Aldehydes Using Copper(II) Catalysis

Author:
Roest, Pjotr C.; Michel, Nicholas W. M.; Batey, Robert A.
Source:
Journal of organic chemistry 2016 v.81 no.15 pp. 6774-6778
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; allylation; catalytic activity; organic chemistry;     Show all 4 Subjects
Abstract:
... The first catalytic method for the selective 1,4-conjugate allylation of α,β-unsaturated aldehydes is reported. The method employs an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent and promotes conjugate addition over 1,2-addition. A variety of aryl- and alkyl-substituted enals are tolerated, providing δ,ε-unsaturated aldehyde products in good yields ...
DOI:
10.1021/acs.joc.6b00782

159. Metal-Free Synthesis of Fully Substituted Pyridines via Ring Construction Based on the Domino Reactions of Enaminones and Aldehydes

Author:
Wan, Jie-Ping; Jing, Yanfeng; Hu, Changfeng; Sheng, Shouri
Source:
Journal of organic chemistry 2016 v.81 no.15 pp. 6826-6831
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical bonding; organic chemistry; pyridines;     Show all 4 Subjects
Abstract:
... An unprecedented domino reaction involving primary enaminones/enaminoesters and aldehydes has been developed for the synthesis of fully substituted pyridines. The construction of the products has been accomplished via the cascade generation of two C–C and one C–N bond by simply using TfOH as a promoter. ...
DOI:
10.1021/acs.joc.6b01149

160. C–ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl Fragment

Author:
Audran, Gérard; Brémond, Paul; Marque, Sylvain R. A.; Yamasaki, Toshihide
Source:
Journal of organic chemistry 2016 v.81 no.5 pp. 1981-1988
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; homolytic cleavage; moieties; organic chemistry; oxidation;     Show all 5 Subjects
Abstract:
... A few years ago, Bagryanskaya and colleagues (J. Org. Chem. 2011) showed that protonation of the nitroxyl fragment deactivated the alkoxyamine C–ON bond. Conversely, our group showed that protonation (Chem. Commun. 2011), as well as other chemical reactions such as oxidation or amine quaternization (Org. Lett. 2012), of the pyridyl moiety carried by the alkyl fragment was suitable to activate the ...
DOI:
10.1021/acs.joc.5b02790

161. Revisited Mechanism of Reaction between a Model Lysine Amino Acid Side Chain and 4-Hydroxynonenal in Different Solvent Environments

Author:
Škulj, Sanja; Vazdar, Katarina; Margetić, Davor; Vazdar, Mario
Source:
Journal of organic chemistry 2018 v.84 no.2 pp. 526-535
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetonitrile; aqueous solutions; chemical reactions; chemical structure; lysine; methylene chloride; models; organic chemistry; pyrroles; quantum mechanics; reaction mechanisms; solvents; thermodynamics; water content;     Show all 15 Subjects
Abstract:
... We revisit the mechanism of reaction between a model lysine side chain and reactive aldehyde 4-hydroxynonenal in different solvents with an increasing water content. We show by model organic reactions and qualitative spectrometric analysis that a nonpolar pyrrole adduct is dominantly formed in non-aqueous solvents dichloromethane and acetonitrile. On the other hand, in aqueous acetonitrile and nea ...
DOI:
10.1021/acs.joc.8b02231

162. Computational Study of Enantioselectivity in the Asymmetric Allylation of Aldehydes with Chiral Pt(II) Phosphinite Complexes

Author:
Dinda, Shrabani
Source:
Journal of organic chemistry 2018 v.83 no.22 pp. 13911-13921
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; allylation; ascorbic acid; carbon; catalysts; chemical bonding; enantioselectivity; hydrogen; ligands; mechanics; moieties; optical isomerism; organic chemistry; oxygen; platinum; prediction; screening;     Show all 17 Subjects
Abstract:
... Computational investigations on the enantioselectivity observed in the allylation of cinnamaldehyde have been carried out using four closely related chiral platinum catalysts with ascorbic acid-based bisphosphinite ligands. Enantioselectivity depends on the substitution of hydrogen on the hydroxyl group by benzyl group(s) in the ascorbic acid framework. The key intermediate is assumed to be one, w ...
DOI:
10.1021/acs.joc.8b02230

163. A Pseudodearomatized PN³P*Ni–H Complex as a Ligand and σ-Nucleophilic Catalyst

Author:
Li, Huaifeng; Gonçalves, Théo P.; Hu, Jinsong; Zhao, Qianyi; Gong, Dirong; Lai, Zhiping; Wang, Zhixiang; Zheng, Junrong; Huang, Kuo-Wei
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14969-14977
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; acylation; alcohols; amines; carbon dioxide; catalytic activity; chemical structure; cycloaddition reactions; dehydrogenation; epoxides; heterocyclic nitrogen compounds; imines; ligands; organic chemistry; organocatalysts;     Show all 16 Subjects
Abstract:
... In contrast to the conventional strategy of modifying the reactivities and selectivities of the transition metal and organocatalysts by varying the steric and electronic properties of organic substituent groups, we hereby demonstrate a novel approach that the sigma (σ) nucleophilicity of the imine arm can be significantly enhanced in a pseudodearomatized PN³P* pincer ligand platform to reach unpre ...
DOI:
10.1021/acs.joc.8b02205

164. Synthesis of α-Arylated Cycloalkanones from Congested Trisubstituted Spiro-epoxides: Application of the House–Meinwald Rearrangement for Ring Expansion

Author:
Jeedimalla, Nagalakshmi; Jacquet, Camille; Bahneva, Diana; Youte Tendoung, Jean-Jacques; Roche, Stéphane P.
Source:
Journal of organic chemistry 2018 v.83 no.20 pp. 12357-12373
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; aluminum chloride; aromatic hydrocarbons; bismuth; carbon; catalytic activity; chemical structure; chemoselectivity; cyclohexanones; epoxidation reactions; feedstocks; organic chemistry; palladium; regioselectivity; synthesis;     Show all 15 Subjects
Abstract:
... A three-step sequence for the synthesis of α-arylated cyclohexanones and the most challenging cycloheptanones is reported. First, an efficient one-pot synthesis of β,β’-disubstituted benzylidene cycloalkanes (styrenes) using the palladium-catalyzed Barluenga reaction from readily available feedstock chemicals is described. Furthermore, an epoxidation followed by the House–Meinwald rearrangement (H ...
DOI:
10.1021/acs.joc.8b01448

165. Selective Hydrogenations and Dechlorinations in Water Mediated by Anionic Surfactant-Stabilized Pd Nanoparticles

Author:
La Sorella, Giorgio; Sperni, Laura; Canton, Patrizia; Coletti, Lisa; Fabris, Fabrizio; Strukul, Giorgio; Scarso, Alessandro
Source:
Journal of organic chemistry 2018 v.83 no.14 pp. 7438-7446
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Bronsted acids; alkenes; alkynes; anionic surfactants; aqueous solutions; catalysts; chemical structure; dechlorination; hydrogen; hydrogenation; ketones; mixing; nanoparticles; organic chemistry; polyethylene glycol; sodium dodecyl sulfonate; sodium dodecylbenzenesulfonate;     Show all 18 Subjects
Abstract:
... We report a facile, inexpensive, and green method for the preparation of Pd nanoparticles in aqueous medium stabilized by anionic sulfonated surfactants sodium 1-dodecanesulfonate 1a, sodium dodecylbenzenesulfonate 1b, dioctyl sulfosuccinate sodium salt 1c, and poly(ethylene glycol) 4-nonylphenyl-3-sulfopropyl ether potassium salt 1d simply obtained by stirring aqueous solutions of Pd(OAc)₂ with t ...
DOI:
10.1021/acs.joc.8b00314

166. Total Synthesis of Ripostatin B and Structure–Activity Relationship Studies on Ripostatin Analogs

Author:
Glaus, Florian; Dedić, Darija; Tare, Priyanka; Nagaraja, Valakunja; Rodrigues, Liliana; Aínsa, José Antonio; Kunze, Jens; Schneider, Gisbert; Hartkoorn, Ruben C.; Cole, Stewart T.; Altmann, Karl-Heinz
Source:
Journal of organic chemistry 2018 v.83 no.13 pp. 7150-7172
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Escherichia coli; Mycobacterium tuberculosis; antibacterial properties; chemical bonding; chemical reactions; enzyme inhibitors; macrolides; moieties; olefin; organic chemistry; oxygen; structure-activity relationships; tuberculosis;     Show all 14 Subjects
Abstract:
... Described is the total synthesis of the myxobacterial natural product ripostatin B and of a small number of analogs. Ripostatin B is a polyketide-derived 14-membered macrolide that acts as an inhibitor of bacterial RNA-polymerase, but is mechanistically distinct from rifamycin-derived RNA-polymerase inhibitors that are in use for tuberculosis treatment. The macrolactone ring of ripostatin B featur ...
DOI:
10.1021/acs.joc.8b00193

167. Multicomponent Catalytic Asymmetric Synthesis of trans-Aziridines

Author:
Zhou, Yubai; Gupta, Anil K.; Mukherjee, Munmun; Zheng, Li; Wulff, William D.
Source:
Journal of organic chemistry 2017 v.82 no.24 pp. 13121-13140
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amines; carbamates; catalysts; chemical reactions; diazo compounds; epoxides; ethers; ethyleneimine; moieties; organic chemistry;     Show all 11 Subjects
Abstract:
... A multicomponent trans-aziridination of aldehydes, amines, and diazo compounds with BOROX catalysts is developed. The optimal protocol is slightly different for aryl aldehydes than for aliphatic aldehydes. The key to the success with aryl aldehydes was allowing the catalyst, aldehyde, and amine to react for 20 min before addition of the diazo compound. A variety of 11 different electron-poor and e ...
DOI:
10.1021/acs.joc.7b02184

168. Bimetallic Cobalt–Rhodium Nanoparticle-Catalyzed Reductive Amination of Aldehydes with Nitroarenes Under Atmospheric Hydrogen

Author:
Choi, Isaac; Chun, Supill; Chung, Young Keun
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12771-12777
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; additives; amination; catalysts; chemical structure; cobalt; hydrogen; nanoparticles; nitroaromatic compounds; organic chemistry; rhodium;     Show all 11 Subjects
Abstract:
... A cobalt–rhodium heterobimetallic nanoparticle (Co₂Rh₂/C)-catalyzed tandem reductive amination of aldehydes with nitroaromatics to sec-amines has been developed. The tandem reaction proceeds without any additives under mild conditions (1 atm H₂ and 25 °C). This procedure can be scaled up to the gram scale, and the catalyst can be reused more than six times without loss of activity. ...
DOI:
10.1021/acs.joc.7b02019

169. Camphorsulfonic Acid Catalyzed One-Pot Three-Component Reaction for the Synthesis of Fused Quinoline and Benzoquinoline Derivatives

Author:
Gattu, Radhakrishna; Bagdi, Prasanta Ray; Basha, R. Sidick; Khan, Abu T.
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12416-12429
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; chemical reactions; chemical structure; ketones; organic chemistry; pregnenolone; quinoline;     Show all 8 Subjects
Abstract:
... A simple and an efficient one-pot three-component reaction of arylamines, aromatic aldehydes, and cyclic ketones was described for the synthesis of various fused quinoline, benzoquinoline, and naphthoquinoline derivatives by using camphorsulfonic acid as a catalyst. The exploitation of pregnenolone steroid for benzoquinolines and terephthalaldehyde for bis-benzoquinolines synthesis was achieved wi ...
DOI:
10.1021/acs.joc.7b02159

170. Iron Catalyzed Hydroboration of Aldehydes and Ketones

Author:
Tamang, Sem Raj; Findlater, Michael
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12857-12862
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; ambient temperature; catalytic activity; chemical reactions; chemical structure; chemoselectivity; iron; ketones; organic chemistry;     Show all 10 Subjects
Abstract:
... We report an operationally convenient room temperature hydroboration of aldehydes and ketones employing Fe(acac)₃ as precatalyst. The hydroboration of aldehydes and ketones proceeded efficiently at room temperature to yield, after work up, 1° and 2° alcohols; chemoselective hydroboration of aldehydes over ketones is attained under these conditions. We propose a σ-bond metathesis mechanism in which ...
DOI:
10.1021/acs.joc.7b02020

171. Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994

Author:
Kim, Miji; Kim, Hyeseung; Kim, Hyunwoo; Chin, Jik
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12050-12058
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; diamines; enantiomers; organic chemistry; stereoselective synthesis; stereoselectivity; temperature;     Show all 8 Subjects
Abstract:
... The stereoselective synthesis of mixed alkyl-aryl vicinal diamines was demonstrated by the use of 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethene (hpen). A sequential addition of aryl and alkyl aldehyde to hpen gave a fused imidazolidine-dihydro-1,3-oxazine ring stereoselectively, which undergoes the diaza-Cope rearrangement to provide mixed vicinal diimines at elevated temperature in good yields and e ...
DOI:
10.1021/acs.joc.7b01751

172. Metal-Free Synthesis of Homopropargylic Alcohols from Aldehydes

Author:
Teodoro, Bruno V. M.; Silva, Luiz F.
Source:
Journal of organic chemistry 2017 v.82 no.22 pp. 11787-11791
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; botulinum toxin; carbon; chemical reactions; chemical structure; iodine; organic chemistry;     Show all 8 Subjects
Abstract:
... The synthesis of homopropargylic alcohols under metal-free and mild condition is described. This transformation is based on a one-pot procedure involving sequential α-alkynylation of acyclic aldehydes using hypervalent iodine reagents and borohydride reduction. The chemistry exhibits broad substrate scope and good scalability, providing a convenient route for the α-alkynylation of aldehydes along ...
DOI:
10.1021/acs.joc.7b01629

173. Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones

Author:
Yu, Subeen; Cho, Eunjeong; Kim, Jimin; Lee, Sunwoo
Source:
Journal of organic chemistry 2017 v.82 no.20 pp. 11150-11156
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetylene; alcohols; carboxylic acids; catalytic activity; chemical reactions; chemical structure; chlorides; organic chemistry; palladium; phosphine;     Show all 11 Subjects
Abstract:
... A palladium-catalyzed decarboxylative coupling reaction was developed for the synthesis of 3-(1-alkynyl)-2-cyclohexen-1-ones. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to afford the corresponding enynones in good to excellent yields. The developed catalytic system is phosphine free and showed good tolerance toward various functionalities such as chloride, ...
DOI:
10.1021/acs.joc.7b02175

174. Base-Mediated Synthesis of Unsymmetrical 1,3,5-Triazin-2-amines via Three-Component Reaction of Imidates, Guanidines, and Amides or Aldehydes

Author:
Pan, Liyang; Li, Zhenxing; Ding, Tao; Fang, Xiaomin; Zhang, Wenkai; Xu, Hao; Xu, Yuanqing
Source:
Journal of organic chemistry 2017 v.82 no.19 pp. 10043-10050
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; amides; catalysts; cesium; chemical reactions; guanidines; imidoesters; moieties; organic chemistry;     Show all 9 Subjects
Abstract:
... A simple and efficient method for the base-mediated synthesis of unsymmetrical 1,3,5-triazin-2-amines has been developed. The protocol uses readily available imidates, guanidines, and amides or aldehydes as the starting materials, cesium carbonate as the base, no catalyst or additive is required, and the three-component reaction provides diverse 1,3,5-triazin-2-amines in moderate to good yields wi ...
DOI:
10.1021/acs.joc.7b01510

175. Reaction of Silyllithium, α-Keto N-tert-Butanesulfinyl Imidates and Aldehydes for Asymmetric Synthesis of α-Substituted β-(Silyloxy)-α-hydroxy Acid Derivatives

Author:
Huang, Wei; Liu, Hui; Xu, Yan-Jun; Lu, Chong-Dao
Source:
Journal of organic chemistry 2017 v.82 no.19 pp. 10748-10755
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis bases; chemical reactions; chemical structure; diastereoselective synthesis; diastereoselectivity; imidoesters; organic chemistry;     Show all 8 Subjects
Abstract:
... A single-flask reaction of silyllithium, α-keto N-tert-butanesulfinyl imidates and aldehydes has been developed for the diastereoselective synthesis of α,β-dihydroxy acid derivatives. In this reaction, the nucleophilic addition of silyllithium to chiral α-keto imidates followed by silyl migration forms chiral aza-enolates, which react diastereoselectively with aldehydes. Subsequent [1,4]-O → O sil ...
DOI:
10.1021/acs.joc.7b02214

176. DMAP-Mediated Synthesis of Fulleropyrrolines: Reaction of [60]Fullerene with Aromatic Aldehydes and Arylmethanamines in the Absence or Presence of Manganese(III) Acetate

Author:
Peng, Jie; Xiang, Jun-Jun; Wang, Hui-Juan; Li, Fa-Bao; Huang, Yong-Shun; Liu, Li; Liu, Chao-Yang; Asiri, Abdullah M.; Alamry, Khalid A.
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9751-9764
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acetates; chemical reactions; fullerene; manganese; moieties; organic chemistry; reaction mechanisms; tautomers;     Show all 9 Subjects
Abstract:
... A series of scarce fulleropyrrolines were synthesized via DMAP-mediated one-step reaction of [60]fullerene with commercially inexpensive aromatic aldehydes and arylmethanamines in the absence or presence of manganese(III) acetate. In the case of aminodiphenylmethane, novel 2,5,5-trisubstituted fulleropyrrolines could be easily obtained without the addition of manganese(III) acetate. As for arylmet ...
DOI:
10.1021/acs.joc.7b01968

177. Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols†

Author:
Umaña, Christian A.; Cabezas, Jorge A.
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9505-9514
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; catalytic activity; chemical reactions; chemical structure; halides; ketones; lithium; magnesium; organic chemistry; palladium; regioselectivity;     Show all 12 Subjects
Abstract:
... Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols an ...
DOI:
10.1021/acs.joc.7b01529

178. Transition-Metal-Free Cascade Approach toward 2-Alkoxy/2-Sulfenylpyridines and Dihydrofuro[2,3-b]pyridines by Trapping In Situ Generated 1,4-Oxazepine

Author:
Cheng, Guolin; Xue, Lulu; Weng, Yunxiang; Cui, Xiuling
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9515-9524
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; ambient temperature; byproducts; chemical structure; cyclization reactions; organic chemistry; pyridines; thiols; trapping;     Show all 10 Subjects
Abstract:
... An efficient cascade reaction via trapping in situ generated active intermediate 1,4-oxazepine, formed from base-promoted 7-exo-dig cyclization reaction of N-propargyl enaminone, has been developed. Alcohols/thiols and aldehydes were used as trapping agents, providing 2-alkoxy/2-sulfenylpyridines and dihydrofuro[2,3-b]pyridines in moderate to high yields. This cascade reaction was completed within ...
DOI:
10.1021/acs.joc.7b01541

179. Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate

Author:
Tan, Zheng; Zhang, Shiwei; Zhang, Yan; Li, Yunpeng; Ni, Minjie; Feng, Bainian
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9384-9399
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; cost effectiveness; methodology; organic chemistry; sodium;     Show all 7 Subjects
Abstract:
... A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois’s reagent (CF₃SO₂Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in in ...
DOI:
10.1021/acs.joc.7b01359

180. Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid

Author:
Luo, Shipeng; Zhang, Xiao; Zheng, Yu; Harms, Klaus; Zhang, Lilu; Meggers, Eric
Source:
Journal of organic chemistry 2017 v.82 no.17 pp. 8995-9005
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis acids; catalysts; chemical structure; enantioselectivity; imidazoles; ketones; optical isomerism; organic chemistry;     Show all 9 Subjects
Abstract:
... The enantioselective catalytic alkynylation of aromatic aldehydes is reported using a sterically highly hindered bis-cyclometalated rhodium-based Lewis acid catalyst featuring the octahedral metal as the only stereogenic center. Yields of 58–98% with 79–98% enantiomeric excess were achieved using 1–2 mol % of catalyst. This work complements previous work from our laboratory on the enantioselective ...
DOI:
10.1021/acs.joc.7b01394

181. Rh-Catalyzed Regioselective ortho-C–H Carbenoid Insertion of Diarylazines

Author:
Yu, Yunliang; Kuai, Changsheng; Chauvin, Remi; Tian, Nian; Ma, Shuangshuang; Cui, Xiuling
Source:
Journal of organic chemistry 2017 v.82 no.16 pp. 8611-8616
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; ambient temperature; chemical structure; diazo compounds; hydrolysis; ketones; organic chemistry; regioselectivity;     Show all 8 Subjects
Abstract:
... The Rh-catalyzed ortho-C–H carbenoid insertion reaction of diarylazines with diazo compounds has been developed. A wide range of ortho-substituted diarylazines have been obtained in moderate to high yields with high regioselectivity at room temperature. The hydrolysis of the products could release ketones or aldehydes, giving access to aromatic 1,5-keto-diesters as valuable synthons for further ch ...
DOI:
10.1021/acs.joc.7b01472

182. Synthesis of 2-Aryl-5-alkyl-fulleropyrrolidines: Metal-Free-Mediated Reaction of [60]Fullerene with Aromatic Aldehydes and Inactive Primary Amines

Author:
Zhang, Meng; Wang, Hui-Juan; Li, Fa-Bao; Zhong, Xin-Xin; Huang, Yong-Shun; Liu, Li; Liu, Chao-Yang; Asiri, Abdullah M.; Alamry, Khalid A.
Source:
Journal of organic chemistry 2017 v.82 no.16 pp. 8617-8627
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chromatography; cis-trans isomers; fullerene; organic chemistry; primary amines;     Show all 7 Subjects
Abstract:
... The metal-free-mediated thermal reaction of [60]fullerene with aromatic aldehydes and inactive primary amines bearing electron-donating groups at the α-position afforded a series of 2-aryl-5-alkyl-fulleropyrrolidines, including the scarce 2-aryl-5-benzyl-fulleropyrrolidines as a mixture of cis and trans isomers. With rare exceptions, the mixture of cis and trans isomers could be easily isolated by ...
DOI:
10.1021/acs.joc.7b01507

183. Nitroalkenes as Latent 1,2-Biselectrophiles – A Multicatalytic Approach for the Synthesis of 1,4-Diketones and Their Application in a Four-Step One-Pot Reaction to Polysubstituted Pyrroles

Author:
Fuchs, Patrick J. W.; Zeitler, Kirsten
Source:
Journal of organic chemistry 2017 v.82 no.15 pp. 7796-7805
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalytic activity; chemical reactions; chemical structure; hydrogen bonding; nitroalkenes; organic chemistry; pyrroles;     Show all 8 Subjects
Abstract:
... An NHC-catalyzed nitro-Stetter/elimination/Stetter reaction sequence employs nitroalkenes as latent 1,2-dication synthons providing a novel access to highly useful symmetrical and unsymmetrical 2-aryl substituted 1,4-diketone building blocks from commercially available aldehyde precursors. For less activated (aliphatic) aldehydes, a cooperative catalytic strategy has been developed via the merger ...
DOI:
10.1021/acs.joc.7b00830

184. Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations

Author:
Pujol, Alba; Whiting, Andrew
Source:
Journal of organic chemistry 2017 v.82 no.14 pp. 7265-7279
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalysts; chemical structure; diastereoselectivity; esters; hydrolysis; imines; organic chemistry; oxidation; stereochemistry; trapping;     Show all 11 Subjects
Abstract:
... Homoallylic boronate carboxylate esters derived from unsaturated aldehydes via an imination, β-borylation, imine hydrolysis, and Wittig trapping sequence, were subjected to a second boryl addition to give 1,3-diborylated carboxylate esters. Control of the absolute and relative stereochemistry of the two new 1,3-stereogenic centers was achieved through: (1) direct chiral catalyst controlled asymmet ...
DOI:
10.1021/acs.joc.7b00854

185. Copper-Catalyzed Radical Cascade Difluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes: A Route to Difluoromethylated Naphthoquinones

Author:
Zhang, Yan; Ye, Shangyi; Ji, Mingming; Li, Lisha; Guo, Dongmei; Zhu, Gangguo
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6811-6818
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkynes; chemical reactions; chemical structure; free radicals; indans; naphthoquinones; organic chemistry;     Show all 8 Subjects
Abstract:
... A novel copper-catalyzed cascade difluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes has been developed. This method affords an efficient and straightforward access to structurally diverse difluoromethylated naphthoquinones in one pot, starting from readily available starting materials. The reaction represents the first trans-acyldifluoromethylation of internal alkynes, which feat ...
DOI:
10.1021/acs.joc.7b00964

186. (E)- and (Z)-Stereodefined Enol Sulfate Esters Derived from α-Aryl Aldehydes: Stereocomplementary Synthesis of Styryl Sulfate Natural Products

Author:
Yu, Shuai; Li, Feng; Kim, Sanghee
Source:
Journal of organic chemistry 2017 v.82 no.13 pp. 6992-6999
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; enols; esters; moieties; organic chemistry; stereoselectivity; sulfates; trapping;     Show all 9 Subjects
Abstract:
... A method for the stereoselective formation of enol sulfate esters from α-aryl aldehydes is described. This method involved the stereocontrolled enolization of a carbonyl group with DBU or t-BuOK followed by trapping with a reactive sulfuryl imidazolium salt, providing the corresponding styryl enol sulfate esters in good to excellent yields and stereoselectivities. This method was applied to the fi ...
DOI:
10.1021/acs.joc.7b00868

187. Diastereoselective [3 + 2] vs [4 + 2] Cycloadditions of Nitroprolinates with α,β-Unsaturated Aldehydes and Electrophilic Alkenes: An Example of Total Periselectivity

Author:
Selva, Verónica; Larrañaga, Olatz; Castelló, Luis M.; Nájera, Carmen; Sansano, José M.; de Cózar, Abel
Source:
Journal of organic chemistry 2017 v.82 no.12 pp. 6298-6312
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis acids; chemical reactions; chemical structure; cyclohexenes; diastereoselectivity; esters; hydrogen; nitroalkenes; organic chemistry; pyrrolidines;     Show all 11 Subjects
Abstract:
... Diastereoselective multicomponent reactions of enantioenriched 4-nitroprolinates, obtained by enantiocatalyzed 1,3-dipolar cycloaddition (1,3-DC) of imino esters and nitroalkenes, with α,β-unsaturated aldehydes and electrophilic alkenes proceed with total periselectivity depending on the structure of the aldehyde employed. This process evolves through a [3 + 2] 1,3-DC when cinnamaldehyde is used i ...
DOI:
10.1021/acs.joc.7b00903

188. Diastereoselectivity of Azido-Ugi Reaction with Secondary Amines. Stereoselective Synthesis of Tetrazole Derivatives

Author:
Zarezin, Danil P.; Khrustalev, Victor N.; Nenajdenko, Valentine G.
Source:
Journal of organic chemistry 2017 v.82 no.12 pp. 6100-6107
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; diastereoselectivity; organic chemistry; piperidines; secondary amines; stereoselective synthesis;     Show all 8 Subjects
Abstract:
... The diastereoselectivity of azido-Ugi reaction with cyclic amines was investigated. It was found that the reaction with α-substituted five- to seven-membered cyclic amines proceeds very efficiently to provide high control of diastereoselectivity (≤100% de) under mild conditions. Target tetrazole-derived products were isolated in excellent yields (≤98%). The reaction has a broad scope in terms of i ...
DOI:
10.1021/acs.joc.7b00611

189. Chemoselective Reduction of Azlactones Using Schwartz’s Reagent

Author:
Pinheiro, Danielle L. J.; Ávila, Eloah P.; Batista, Gabriel M. F.; Amarante, Giovanni W.
Source:
Journal of organic chemistry 2017 v.82 no.11 pp. 5981-5985
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; ambient temperature; chemical reactions; chemical structure; chemoselectivity; organic chemistry;     Show all 7 Subjects
Abstract:
... Highly chemoselective addition of Schwartz’s reagent to widely available azlactones is described. This method allows the preparation of challenged functionalized α-amino aldehydes, in good to high isolated yields at room temperature, after only 2 min reaction. The presence of sensitive functionalities or electronic factors does not compromise the potential of the method. The use of an excess of th ...
DOI:
10.1021/acs.joc.7b00820

190. Dehydrogenative Transformations of Imines Using a Heterogeneous Photocatalyst

Author:
Adolph, Colby M.; Werth, Jacob; Selvaraj, Ramajeyam; Wegener, Evan C.; Uyeda, Christopher
Source:
Journal of organic chemistry 2017 v.82 no.11 pp. 5959-5965
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; dehydrogenation; imines; moieties; organic chemistry; photocatalysts; redox reactions; semiconductors; titanium dioxide;     Show all 10 Subjects
Abstract:
... Heterogeneous semiconductors are underexploited as photoredox catalysts in organic synthesis relative to their homogeneous, molecular counterparts. Here, we report the use of metal/TiO₂ particles as catalysts for light-induced dehydrogenative imine transformations. The highly oxophilic nature of the TiO₂ surface promotes the selective binding and dehydrogenation of alcohols in the presence of othe ...
DOI:
10.1021/acs.joc.7b00617

191. Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes

Author:
Yue, Yixia; Peng, Jinsong; Wang, Deqiang; Bian, Yunyun; Sun, Peng; Chen, Chunxia
Source:
Journal of organic chemistry 2017 v.82 no.10 pp. 5481-5486
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acylation; bromides; catalysts; catalytic activity; chemical structure; flavonoids; organic chemistry; palladium; potassium carbonate;     Show all 10 Subjects
Abstract:
... The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh₃)₄/Xphos as the catalyst and K₂CO₃ as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane. ...
DOI:
10.1021/acs.joc.7b00640

192. Catalytic, Enantioselective β-Protonation through a Cooperative Activation Strategy

Author:
Wang, Michael H.; Barsoum, David; Schwamb, C. Benjamin; Cohen, Daniel T.; Goess, Brian C.; Riedrich, Matthias; Chan, Audrey; Maki, Brooks E.; Mishra, Rama K.; Scheidt, Karl A.
Source:
Journal of organic chemistry 2017 v.82 no.9 pp. 4689-4702
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acylation; alcohols; catalysts; catalytic activity; chemical structure; enantioselectivity; esters; hydrogen bonding; organic chemistry; solvents;     Show all 11 Subjects
Abstract:
... The NHC-catalyzed transformation of unsaturated aldehydes into saturated esters through an organocatalytic homoenolate process has been thoroughly studied. Leveraging a unique “Umpolung”-mediated β-protonation, this process has evolved from a test bed for homoenolate reactivity to a broader platform for asymmetric catalysis. Inspired by our success in using the β-protonation process to generate en ...
DOI:
10.1021/acs.joc.7b00334

193. Cross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D−π–A Organic Dyes: C–H/C–H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications

Author:
Ciou, Yan-Syun; Lin, Po-Han; Li, Wei-Ming; Lee, Kun-Mu; Liu, Ching-Yuan
Source:
Journal of organic chemistry 2017 v.82 no.7 pp. 3538-3551
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; catalytic activity; chemical reactions; dyes; moieties; organic chemistry; photovoltaic cells;     Show all 7 Subjects
Abstract:
... A variety of push–pull type organic dyes are facilely synthesized through the most atom-economical C–H/C–H dehydrogenative coupling reactions. After comprehensive synthetic optimizations, a broad substrate scope is achieved and functional groups, such as ester, ketone, nitrile, nitro, and triazene are well tolerated. The sensitive aldehyde group required for the conversion into anchoring groups fo ...
DOI:
10.1021/acs.joc.7b00054

194. Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization

Author:
Nishino, Kota; Minato, Kohei; Miyazaki, Takahiro; Ogiwara, Yohei; Sakai, Norio
Source:
Journal of organic chemistry 2017 v.82 no.7 pp. 3659-3665
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; carboxylic acids; catalysts; chemical reactions; chemical structure; desulfurization; indium; organic chemistry;     Show all 8 Subjects
Abstract:
... In this study an InI₃-TMDS (1,1,3,3-tetramethyldisiloxane) reducing system effectively catalyzed the reductive dithioacetalization of a variety of aromatic and aliphatic carboxylic acids with 1,2-ethanedithiol or 1,3-propanedithiol leading to the one-pot preparation of either 1,3-dithiolane derivatives or a 1,3-dithiane derivative. Also, the intact indium catalyst continuously catalyzed the subseq ...
DOI:
10.1021/acs.joc.7b00170

195. Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation

Author:
Martins, Bruna S.; Moro, Angélica V.; Lüdtke, Diogo S.
Source:
Journal of organic chemistry 2017 v.82 no.6 pp. 3334-3340
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; acids; arylation; chelation; enantiomers; nitrogen; organic chemistry; stereochemistry; stereoselectivity; zinc;     Show all 10 Subjects
Abstract:
... The chelation-controlled arylation reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et₂Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin–Anh contr ...
DOI:
10.1021/acs.joc.7b00215

196. One-Pot Synthesis of Indoles by a Sequential Ugi-3CR/Wittig Reaction Starting from Odorless Isocyanide-Substituted Phosphonium Salts

Author:
Yan, Yan-Mei; Rao, Yong; Ding, Ming-Wu
Source:
Journal of organic chemistry 2017 v.82 no.5 pp. 2772-2776
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; chemical reactions; chemical structure; indoles; organic chemistry; phosphoric acid; potassium carbonate; synthesis;     Show all 8 Subjects
Abstract:
... A new one-pot preparation of indoles by a Ugi-3CR/Wittig sequence has been developed. The reaction of odorless isocyanide-substituted phosphonium salt 5, aldehyde 6, and amine 7 produced the indoles 9 in 45–82% yields via a sequential Ugi-3CR/Wittig reaction in the presence of H₃PO₄ and solid K₂CO₃, respectively. ...
DOI:
10.1021/acs.joc.7b00004

197. Reaction of Aldehydes/Ketones with Electron-Deficient 1,3,5-Triazines Leading to Functionalized Pyrimidines as Diels–Alder/Retro-Diels–Alder Reaction Products: Reaction Development and Mechanistic Studies

Author:
Yang, Kai; Dang, Qun; Cai, Pei-Jun; Gao, Yang; Yu, Zhi-Xiang; Bai, Xu
Source:
Journal of organic chemistry 2017 v.82 no.5 pp. 2336-2344
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; Lewis acids; chemical structure; cycloaddition reactions; ethers; ketones; organic chemistry; pyrimidines; reaction mechanisms;     Show all 9 Subjects
Abstract:
... Catalytic inverse electron demand Diels–Alder (IEDDA) reactions of heterocyclic aza-dienes are rarely reported since highly reactive and electron-rich dienophiles are often found not compatible with strong acids such as Lewis acids. Herein, we disclose that TFA-catalyzed reactions of electron-deficient 1,3,5-triazines and electron-deficient aldehydes/ketones can take place. These reactions led to ...
DOI:
10.1021/acs.joc.6b02570

198. Sequential Carbon–Carbon/Carbon–Selenium Bond Formation Mediated by Iron(III) Chloride and Diorganyl Diselenides: Synthesis and Reactivity of 2-Organoselenyl-Naphthalenes

Author:
Recchi, Ana M. S.; Back, Davi F.; Zeni, Gilson
Source:
Journal of organic chemistry 2017 v.82 no.5 pp. 2713-2723
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alcohols; aromatic compounds; bromides; chemical structure; chlorides; cyclization reactions; iron; organic chemistry; sulfides; trapping;     Show all 11 Subjects
Abstract:
... In this paper, we report an intramolecular cyclization of benzylic-substituted propargyl alcohols promoted by iron(III) chloride and diorganyl diselenides to give 2-organoselenyl-naphthalenes via a sequential carbon–carbon/carbon–selenium bond formation. The present reaction tolerated a wide range of substituents in both propargyl alcohols and diorganyl diselenides to give the desired 2-organosele ...
DOI:
10.1021/acs.joc.7b00050

199. Desymmetrizing Hydroformylation of Dihydromuconic Acid Diesters: Application to the Synthesis of (±)-Vindeburnol

Author:
Salacz, Laura; Charpentier, Cyrille; Suffert, Jean; Girard, Nicolas
Source:
Journal of organic chemistry 2017 v.82 no.4 pp. 2257-2262
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; alkenes; chemical reactions; chemical structure; organic chemistry; primary amines; tryptamine;     Show all 7 Subjects
Abstract:
... The desymmetrizing hydroformylation of internal alkenes derived from dihydromuconic acid is described. The study of this reaction afforded easy access to polyfunction aldehydes. After the evaluation of the reactivity of the dimethyl ester derivative with various primary amines, this methodology was used to design a rapid synthesis of (±)-vindeburnol from tryptamine in only two steps. ...
DOI:
10.1021/acs.joc.6b02939

200. A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2-Amino-2-vinyl-1,3-diols

Author:
Rodríguez, Aleix; Ariza, Xavier; Contreras, Miguel A.; Garcia, Jordi; Lloyd-Williams, Paul; Mercadal, Nerea; Sánchez, Carolina
Source:
Journal of organic chemistry 2017 v.82 no.3 pp. 1851-1855
ISSN:
1520-6904
Subject:
aldehydes,   etc   ; allene; chemical reactions; chemical structure; organic chemistry; stereochemistry; stereoselective synthesis;     Show all 7 Subjects
Abstract:
... Treatment of readily available allene 1 with Cy₂BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected. ...
DOI:
10.1021/acs.joc.6b02765