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You searched for: Journal name Journal of organic chemistry Remove constraint Journal name: Journal of organic chemistry Publication year rev 7982-2018 Remove constraint Publication year rev: 7982-2018 Source 2018 v.83 no.24 Remove constraint Source: 2018 v.83 no.24
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1. 1,3-Dioxa-[3,3]-sigmatropic Oxo-Rearrangement of Substituted Allylic Carbamates: Scope and Mechanistic Studies

Author:
Maddalen Agirre; Sylvain Henrion; Ivan Rivilla; José I. Miranda; Fernando P. Cossío; Bertrand Carboni; José M. Villalgordo; François Carreaux
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14861-14881
ISSN:
1520-6904
Subject:
alcohols; aromatic compounds; carbamates; chemical reactions; chemical structure; kinetics; organic chemistry
Abstract:
... An unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment of aryl- and alkenyl-substituted allylic alcohols with activated isocyanates is reported. The reorganization of bonds is highly dependent on the electron density of the aromatic ring and the nature of isocyanate used. This metal-free tandem reaction from branched allyl alcohols initiated by a carbamoylation reaction and f ...
DOI:
10.1021/acs.joc.8b01320

2. Alkaloids Reactivity: DFT Analysis of Selective Demethylation Reactions

Author:
Olatz Larrañaga; José I. Miranda; Fernando P. Cossío; Abel de Cózar
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15101-15109
ISSN:
1520-6904
Subject:
alkaloids; chemical reactions; chemical structure; demethylation; organic chemistry; theoretical models
Abstract:
... All possible demethylation reactions of a diverse family of quaternary alkaloids by means of DFT calculations are here described. We aim to develop a rational model that allows the explanation of the high selectivity observed experimentally and predicts the occurrence of new alkaloid derivatives. To this end, we have performed a detailed analysis of the initial reagents and products. In addition, ...
DOI:
10.1021/acs.joc.8b02364

3. Atomic Charges

Author:
Kenneth B. Wiberg; Paul R. Rablen
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15463-15469
ISSN:
1520-6904
Subject:
acidity; chemical reactions; chemical structure; energy; gases; hydrogen; hydrogen bonding; methanol; models; organic chemistry
Abstract:
... The problem of deriving atomic charges from the results of ab Initio MO calculations has been studied by the use of several reported methods: Mulliken population analysis, the minimal basis set (MBS) procedure, the natural population analysis (NPA), two electrostatic potential fitting methods, M-K and ChelpG, the Hirshfeld population analysis, and CM5 (charge model 5), which is related to the Hirs ...
DOI:
10.1021/acs.joc.8b02740

4. Can the Radical Channel Contribute to the Catalytic Cycle of N-Heterocyclic Carbene in Benzoin Condensation?

Author:
Ming-Hsiu Hsieh; Gou-Tao Huang; Jen-Shiang K. Yu
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15202-15209
ISSN:
1520-6904
Subject:
benzaldehyde; carbenes; catalytic activity; chemical structure; electron paramagnetic resonance spectroscopy; heterocyclic nitrogen compounds; hydrogen; organic chemistry; tautomerization
Abstract:
... NHC can catalyze benzoin condensation via the key Breslow intermediate. EPR spectroscopy recently confirmed the existence of the radical species, but its catalytic role is still unclear. Herein, we use density functional approaches to study the radical-associated pathway in comparison with the nonradical mechanism reported previously. Theoretical investigations show that the nonradical path (ΔG⧧ = ...
DOI:
10.1021/acs.joc.8b02483

5. Chiroptical Inversion of Europium(III) Complexes by Changing a Remote Stereogenic Center of a C₂-Symmetric Bispyrrolidinoindoline Manifold

Author:
Tomoaki Taniguchi; Akira Tsubouchi; Yuki Imai; Junpei Yuasa; Hiroki Oguri
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15284-15296
ISSN:
1520-6904
Subject:
chemical reactions; chemical structure; europium; ligands; luminescence; organic chemistry; pyridines
Abstract:
... As an effort to integrate natural products chemistry and coordination chemistry, a diastereomeric pair of chiral alkaloidal manifolds composed of a bispyrrolidinoindoline (BPI) framework was designed and synthesized to generate luminescent Euᴵᴵᴵ complexes with switchable chiroptical properties. The C₂-symmetric alkaloidal manifolds were linked with bis(benzimidazolyl)pyridine (BBIPy) as an achiral ...
DOI:
10.1021/acs.joc.8b02550

6. Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature

Author:
Mingchuang He; Zhaohua Yan; Fuyuan Zhu; Sen Lin
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15438-15448
ISSN:
1520-6904
Subject:
Lewis bases; ambient temperature; chemical bonding; chemical structure; copper; esters; imines; organic chemistry; photocatalysis; sulfides; sulfur; thiols
Abstract:
... A copper-catalyzed iminyl radical-mediated C–C bond cleavage/cross-coupling tandem reaction of cyclobutanone oxime esters with aryl thiols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature was developed, and aryl cyanopropyl sulfides were smoothly synthesized in 20–88% yields. By altering the copper reagent and the molar ratio of cyclobutanone oxime ester/aryl thiol/D ...
DOI:
10.1021/acs.joc.8b02707

7. Copper-Catalyzed Domino Addition, Hydroamination, and Cyclization: A Multicomponent Approach to Spiro Oxazolidinone Derivatives

Author:
Gal Reddy Potuganti; Divakar Reddy Indukuri; Jagadeesh Babu Nanubolu; Manjula Alla
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15186-15194
ISSN:
1520-6904
Subject:
chemical bonding; chemical reactions; chemical structure; ketones; organic chemistry; oxazolidinones
Abstract:
... A copper-catalyzed one-pot multicomponent protocol has been developed for construction of spiro heterocycles. The domino approach leads to the synthesis of spiro oxazolidinones starting from ketones, arylacetylenes, and isocyanates via catalytic addition, hydroamination, and cyclization involving consecutive C–C, C–O, and C–N bond formations. ...
DOI:
10.1021/acs.joc.8b02461

8. Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Furo[3,2-a]carbazole Alkaloid Furoclausine-B

Author:
Benedikt Spindler; Olga Kataeva; Hans-Joachim Knölker
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15136-15143
ISSN:
1520-6904
Subject:
alkaloids; chemical bonding; enantioselectivity; epoxidation reactions; moieties; organic chemistry; palladium
Abstract:
... We describe the first enantioselective total synthesis and the assignment of the absolute configuration of the furo[3,2-a]carbazole alkaloid furoclausine-B. As key steps for our approach we used a palladium(II)-catalyzed double C–H-bond activation for the construction of the carbazole framework, a Shi epoxidation, and an intramolecular opening of the epoxide for annulation of the dihydrofuran moie ...
DOI:
10.1021/acs.joc.8b02426

9. Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

Author:
Wei Chen; Renyu Guo; Zhen Yang; Jianxian Gong
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15524-15532
ISSN:
1520-6904
Subject:
chemical structure; dimerization; organic chemistry; quinones
Abstract:
... The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total sy ...
DOI:
10.1021/acs.joc.8b02595

10. One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H₂SO₄-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols

Author:
Vakhid A. Mamedov; Nataliya A. Zhukova; Aidar T. Gubaidullin; Victor V. Syakaev; Milyausha S. Kadyrova; Tat’yana N. Beschastnova; Olga B. Bazanova; Il′dar Kh. Rizvanov; Shamil K. Latypov
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14942-14953
ISSN:
1520-6904
Subject:
Lewis bases; benzimidazole; chemical reactions; chemical structure; fluorine; nitrogen; organic chemistry; reaction mechanisms; synthesis
Abstract:
... A facile approach to a range of substituted 7-(benzimidazol-2-yl)thioxolumazines [7-(benzimidazol-2-yl)-2-thioxo-2,3-dihydropteridin-4(1H)-ones] and 7-(benzimidazol-2-yl)lumazines [7-(benzimidazol-2-yl)pteridine-2,4(1H,3H)-diones] is described. These new biheterocyclic systems are obtained via H₂SO₄-catalyzed rearrangement of quinoxalin-2-ones in the presence of 5,6-diamino-2-mercapto- and 2,5,6-t ...
DOI:
10.1021/acs.joc.8b02161

11. Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki–Miyaura Cross-Coupling in Water and Air

Author:
Szilvia Bunda; Antal Udvardy; Krisztina Voronova; Ferenc Joó
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15486-15492
ISSN:
1520-6904
Subject:
Suzuki reaction; active pharmaceutical ingredients; aerobic conditions; air; catalysts; chemical structure; filtration; hydrochloric acid; organic chemistry; organic compounds; palladium; washing; water solubility
Abstract:
... With use of a Pd(II)-sulfosalan complex as a water-soluble catalyst, we have developed an efficient synthesis of biaryls via Suzuki–Miyaura cross-coupling in water under aerobic conditions. The water-insoluble target molecules were isolated by simple filtration in analytical purity after washing with 0.01 M aqueous HCl (20 examples). In most cases, palladium contamination was below 5 ppm considere ...
DOI:
10.1021/acs.joc.8b02340

12. Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose

Author:
Lin-E Guo; Yuan Hong; Shu-Ying Zhang; Miao Zhang; Xiao-Sheng Yan; Jin-Lian Cao; Zhao Li; Tony D. James; Yun-Bao Jiang
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15128-15135
ISSN:
1520-6904
Subject:
carboxylic acids; chemical reactions; chemical structure; glucose; models; nuclear magnetic resonance spectroscopy; organic chemistry; phenylboronic acids; proline; receptors
Abstract:
... Chiral recognition remains a major challenge in the area of molecular receptor design. With this research, we set out to explore the use of proline-based receptors for chiral recognition. Importantly, the proline structure allows for the introduction of at least two different binding groups due to the availability of both an amine and carboxylic acid group. Here we report a proof-of-concept explor ...
DOI:
10.1021/acs.joc.8b02425

13. Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles

Author:
Sebastian Koller; Julia Gatzka; Kit Ming Wong; Philipp J. Altmann; Alexander Pöthig; Lukas Hintermann
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15009-15028
ISSN:
1520-6904
Subject:
Grignard reagents; Lewis acids; air; carboxylation; carboxylic acids; chemical bonding; deuterium; deuterium oxide; diastereomers; hydrolysis; nuclear magnetic resonance spectroscopy; organic chemistry; organochlorine compounds; phosphorus; stable isotopes; stereochemistry; thermodynamics
Abstract:
... Menthyl Grignard reagent 1 from either menthyl chloride (2) or neomenthyl chloride (3) consists of menthylmagnesium chloride (1a), neomenthylmagnesium chloride (1b), trans-p-menthane (4), 2-menthene (8), 3-menthene (9), and Wurtz coupling products including symmetrical bimenthyl 13. The diastereomeric ratio 1a/1b was determined in situ by ¹³C NMR or after D₂O quenching by ²H NMR analysis. Hydrolys ...
DOI:
10.1021/acs.joc.8b02278

14. Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration

Author:
Ivan Sivák; Michal Toběrný; Andrea Kyselicová; Ol’ga Caletková; Dušan Berkeš; Pavol Jakubec; Andrej Kolarovič
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15541-15548
ISSN:
1520-6904
Subject:
acids; amino acids; chemical reactions; diastereomers; filtration; organic chemistry; organic compounds; stereochemistry; stereoselective synthesis
Abstract:
... Crystallization-induced diastereomer transformation (CIDT) represents a highly appealing and convenient synthetic tool. Despite its numerous advantages, it remains rather rarely used due to its uncertain predictability to occur. Herein, we describe CIDT based on aza-Michael reactions of diversely functionalized (E)-3-acylacrylic acids. This method provides direct access to a broad variety of α-ami ...
DOI:
10.1021/acs.joc.8b02647

15. Synthesis and Evaluation of 1,5-Dithia-d-laminaribiose, Triose, and Tetraose as Truncated β-(1→3)-Glucan Mimetics

Author:
Xiaoxiao Liao; Václav Větvička; David Crich
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14894-14904
ISSN:
1520-6904
Subject:
antibodies; carbohydrate binding; chemical bonding; chemical reactions; chemical structure; fluorescence; humans; hydrophobicity; macrophages; mice; neutrophils; organic chemistry; organic compounds; oxygen; phagocytosis; staining; trisaccharides
Abstract:
... The preparation and characterization of a series of di-, tri-, and tetrasaccharide analogues of β-(1→3)-glucans is described in which each pyranoside ring is replaced by a 5-thiopyranosyl ring and each glycosidic oxygen by a thioether. These oligomeric 1,5-dithio-d-glucopyranose derivatives were shown to inhibit the staining of human neutrophils and of mouse macrophages by fluorescent anti-CR3 and ...
DOI:
10.1021/acs.joc.8b01645
PubMed:
30456952
PubMed Central:
PMC6467787

16. Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Author:
Swarup De; Amit M. Jabgunde; Rahul S. Patil; Steven De Jonghe; Leonid Beigelman; Piet Herdewijn
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15155-15169
ISSN:
1520-6904
Subject:
azides; chemical reactions; chemical structure; ethylene oxide; nucleic acids; nucleosides; oligonucleotides; organic chemistry; regioselectivity; uracil
Abstract:
... A new synthesis protocol for the preparation of hitherto unknown 1′,5′-anhydro-4′-amino-trityl/MMTr hexitol nucleosides has been developed. Key steps in the synthesis of the pyrimidine analogues (U and C) include the regioselective d-allo-hexitol oxirane and 2′,4′-anhydronucleoside ring opening by uracil and azide, respectively. A different strategy using a regioselective epoxide ring opening of d ...
DOI:
10.1021/acs.joc.8b02444

17. Total Synthesis of (−)-Mucosin and Revision of Structure

Author:
Jens M. J. Nolsøe; Simen Antonsen; Carl H. Görbitz; Trond V. Hansen; Jannicke I. Nesman; Åsmund K. Røhr; Yngve H. Stenstrøm
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15066-15076
ISSN:
1520-6904
Subject:
chemical structure; organic chemistry; organic compounds; protonation
Abstract:
... The first total synthesis of (−)-mucosin (6), an unusual marine hydrindane natural product incorporating a prostaglandin-like submotif, has been achieved. As a result of the campaign, three of the four all-carbon stereocenters in the purported structure 1 have been revised. Of particular note is the excellent control over β-chirality in conjugate addition to ester (−)-22 and the facial selectivity ...
DOI:
10.1021/acs.joc.8b02318

18. Total Synthesis of epi-Trichosetin

Author:
Ulrich Kauhl; Lars Andernach; Till Opatz
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15170-15177
ISSN:
1520-6904
Subject:
chemical reactions; chemical structure; organic chemistry; organic compounds
Abstract:
... The natural 3-decalinoyltetramic acid epi-trichosetin was synthesized in ten steps starting from (R)-(+)-citronellal using an intramolecular Diels–Alder reaction and a Lacey–Dieckmann cyclization as the key steps. The use of a 2-nitrobenzyl protecting group resulted in an efficient synthetic endgame. The natural product was obtained in 4.1% overall yield. ...
DOI:
10.1021/acs.joc.8b02450

19. [1]Benzothiophene-Fused Chiral Spiro Polycyclic Aromatic Compounds: Optical Resolution, Functionalization, and Optical Properties

Author:
Ko Takase; Keiichi Noguchi; Koji Nakano
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15057-15065
ISSN:
1520-6904
Subject:
X-radiation; aromatic compounds; chemical reactions; enantiomers; fluorescence; high performance liquid chromatography; optical properties; organic chemistry; polycyclic compounds
Abstract:
... Spiro polycyclic aromatic compounds have been known as rigid chiral scaffolds. In order to extend their applications, an efficient preparation route to enantiopure derivatives is highly required. Here, we design 10,10′-spirobi[indeno[1,2-b][1]benzothiophene]-7,7′-diol to achieve efficient optical resolution. The compound was successfully synthesized and resolved by chiral HPLC on a semipreparative ...
DOI:
10.1021/acs.joc.8b02301

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

Author:
Huaifeng Li; Théo P. Gonçalves; Jinsong Hu; Qianyi Zhao; Dirong Gong; Zhiping Lai; Zhixiang Wang; Junrong Zheng; Kuo-Wei Huang
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14969-14977
ISSN:
1520-6904
Subject:
Lewis bases; acylation; alcohols; aldehydes; amines; carbon dioxide; catalytic activity; chemical structure; cycloaddition reactions; dehydrogenation; epoxides; heterocyclic nitrogen compounds; imines; ligands; organic chemistry; organocatalysts
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