Nucleophilic Carbenes in Asymmetric Organocatalysis
Top Cited Papers
- 25 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 37 (8) , 534-541
- https://doi.org/10.1021/ar030050j
Abstract
The coenzyme thiamine (vitamin B1), a natural thiazolium salt, is involved in many enzymatic catalyses. Since it has been proposed that the catalytically active species of these reactions is a nucleophilic carbene, many chemists have tried to perform enzyme mimetic asymmetric carbene catalysis. After a long and difficult search, stable carbenes are finally isolated, characterized, and in the chemist's hands. The experiments of decades have finally resulted in successful enantioselective benzoin condensations and enantioselective intramolecular Stetter reactions as important examples of carbene catalyzed asymmetric nucleophilic acylation processes.Keywords
This publication has 34 references indexed in Scilit:
- Current mechanistic understanding of thiamin diphosphate-dependent enzymatic reactionsNatural Product Reports, 2003
- Synthetic potential of thiamin diphosphate-dependent enzymesJournal of Molecular Catalysis B: Enzymatic, 1999
- The thiazolium catalyzed benzoin condensation with mild base does not involve a “dimer” intermediateTetrahedron Letters, 1994
- New evidence supporting bis(thiazolin-2-ylidene)s as the actual catalytic species in the benzoin condensation.Tetrahedron Letters, 1993
- The benzoin condensation catalysis by bis(azolin-2-ylidene)s and bis(azolidin-2-ylidene)s and its interpretation within the context of nucleophilic carbene chemistryJournal of Heterocyclic Chemistry, 1986
- Electron Pairing and Linear H3+Journal of the American Chemical Society, 1964
- Indanols. I. Preparation and Spectra of Benzylated Indanols1Journal of the American Chemical Society, 1958
- Mechanism of Thiamine-catalyzed Reactions1Journal of the American Chemical Society, 1954
- XCVII.—Resolution of α-benzylmethylacetic acidJournal of the Chemical Society, Transactions, 1903
- Untersuchungen über das Radikal der BenzoesäureEuropean Journal of Organic Chemistry, 1832