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... The base-mediated rearrangement of epoxides into allylic alcohols is a well-known synthetic transformation. The first enantioselective version of the reaction using a chiral base was reported in 1980. Since then, the reaction has received a lot of attention mostly due to the great usefulness of chiral allylic alcohols in organic synthesis. Major breakthroughs in the area were the first report on u ...
... Electrocatalytic cycloaddition of carbon dioxide to epoxides in room temperature ionic liquids as reaction media without any additional supporting electrolyte and catalyst could be conducted with high to excellent performances under mild conditions. ...
aldehydes; carbonyl compounds; catalytic activity; chemical reactions; epoxides; salts
Abstract:
... Triphenylarsine catalyses the formation of epoxides from carbonyl compounds and tosylhydrazone salts. This convergent synthesis gives complete trans selectivity for all aldehyde and tosylhydrazone salt coupling partners. ...
Lewis acids; catalytic activity; chromium; cycloaddition reactions; epoxides; organic chemistry
Abstract:
... An overview focused on the synthesis, structural features and catalytic applications of chiral [Cr(Salen)] complexes is presented. Key aspects of modern organic chemistry such as Lewis acids, asymmetric catalysis and redox processes are strictly connected with chromium–Schiff base complexes. Among the asymmetric transformations mediated by [Cr(Salen)] complexes, Diels–Alder and hetero-Diels–Alder ...
... We have developed a new catalytic solid phase system for epoxidations using urea–hydrogen peroxide complex (urea–H₂O₂) and cetylpyridinium dodecatungstate ((CetylPy)₁₀ [H₂W₁₂O₄₂]) catalyst on fluorapatite. In the solid phase system epoxidations of cyclic alkenes and allylic alcohols proceeded without solvent at room temperature to afford the corresponding epoxides in good yields. The recovered sol ...
... In the chiral Co(iii)(salen)-catalysed HKR of racemic epoxides, in the presence of ionic liquids, Co(ii)(salen) complex is oxidised without acetic acid to catalytically active Co(iii)(salen) complex during reaction and, moreover, this oxidation state is stabilised against reduction to Co(ii) complex which enables the reuse of the recovered catalyst for consecutive reactions without extra reoxidati ...
catalytic activity; epoxides; green chemistry; sodium hydroxide
Abstract:
... An environmentally friendly synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines has been carried out in a sequential fashion through the R₄N⁺F⁻ catalyzed ring opening of epoxides with arylsulfonamides, followed by in situ cyclization of the hydroxysulfonamides thus obtained with NaOH aq. and n-C₁₄H₂₉N⁺Me₃Cl⁻. ...
... Epoxidation of 1-octene with hydrogen peroxide catalysed by amphiphilic salts of peroxo tungstophosphate {PO₄[WO(O₂)₂]₄}³⁻ in water-in-oil microemulsions is an efficient and environmentally benign reaction which, coupled with ultrafiltration, shows the potential for continuous production of epoxides. ...
... The desymmetrization ring opening of meso epoxides using trimethylsilyl cyanide catalyzed by organogallium and indium complexes with binaphthol monoether derivatives as chiral ligands gave β-isocyanohydrins with moderate to excellent enantioselectivities of up to 95% ee. ...
... A cascade epoxide rearrangement–aldehyde allylation was developed by using a combination of InCl and reusable heterogeneous mesoporous silica supported palladium catalysts. ...
catalytic activity; cobalt; copolymerization; epoxides; porous media
Abstract:
... Template copolymerization methods have been utilized to prepare porous materials with immobilized cobalt complexes that catalyze the hydrolytic kinetic resolution of epoxides. ...
... The intent of this tutorial review is to cover the recent progress accomplished in iron and manganese porphyrin-catalyzed enantioselective epoxidation of terminal olefins. The literature is covered up to the beginning of 2005. In the first part of the manuscript, we will present the results obtained with simple catalysts in the early eighties, before describing the pickets and strapped series repo ...
amino alcohols; catalysts; catalytic activity; epoxides; green chemistry; thiols; triethylamine
Abstract:
... Ring-opening of epoxides with various amines or thiols catalyzed by DABCO (1,4-diazabicyclic[2,2,2]octane) or Et₃N (1 mol%) in water afforded the corresponding products in good to excellent yields under mild reaction conditions. ...
Lewis bases; carbon dioxide; catalysts; catalytic activity; chemical reactions; epoxides; hydroxyapatite; solvents; zinc
Abstract:
... A zinc-based hydroxyapatite catalyst in conjunction with a Lewis base proved to be efficient for the coupling of CO₂ and epoxide in the absence of additional organic solvents under an atmospheric CO₂ pressure; the work-up procedure is straightforward and the catalyst could be reused without loss of catalytic activity and selectivity. ...
... Epoxide hydrolases play an important role in the biodegradation of organic compounds and are potentially useful in enantioselective biocatalysis. An analysis of various genomic databases revealed that about 20% of sequenced organisms contain one or more putative epoxide hydrolase genes. They were found in all domains of life, and many fungi and actinobacteria contain several putative epoxide hydro ...
... Under trialkylphosphine catalyzed Morita–Baylis–Hillman reaction conditions, epoxides react with enones to give rise to homologous aldol adducts. ...
... Ionic liquids (ILs) offer new possibilities for epoxide hydrolase (EH) catalyzed resolution of epoxides and for synthesis of chiral 1,2-diols. Soluble EHs from cress and mouse (csEH and msEH) and microsomal EH from rat (rmEH) were tested in several ILs. For all the enzymes tested, higher enantioselectivities were obtained in [bmim][N(Tf)₂] and [bmim][PF₆]. The optimized amount of water for EH acti ...
alcohols; catalysts; catalytic activity; chemoselectivity; epoxides; green chemistry; nanoparticles; palladium
Abstract:
... Hydrogenolysis of various benzylic epoxides was achieved in water to give alcohols in 51–98% yield using recyclable Pd nanoparticles as catalyst. ...
... In this work, the catalytic efficiency of ionic liquid (IL) choline chloride/urea supported on molecular sieves for the reactions of CO₂ and epoxides was studied under different conditions. It was demonstrated that this biodegradable and green catalyst is very active and selective, and choline chloride and urea showed a synergetic effect in promoting these reactions. After reaction, the solid cata ...
... Glycidol is used as an initiator for ring-opening polymerisation of ε-caprolactone (ε-CL) to synthesise epoxy-functionalised poly(ε-caprolactone) (PCL) in a reaction catalysed by lipase, and the epoxy-functionalised PCL was further copolymerised with carbon dioxide or anhydride to produce novel graft or hyperbranched copolymers. ...