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Asymmetric catalysis of aldol reactions with chiral lewis bases.
Acc Chem Res. 2000 Jun; 33(6):432-40.AC

Abstract

In an extension of studies both on the stereochemical course of the aldol addition and on Lewis-base-catalyzed allylation reactions, we have invented a new Lewis-base-catalyzed asymmetric aldol addition. This Account outlines the conceptual development, the identification of design criteria, and the underlying principles for such a process. The reduction of these elements to practice in the demonstration of enantioselective aldol additions of trichlorosilyl enolates catalyzed by chiral phosphoramides is also presented. From a combination of stereochemical, kinetic, and structural studies, an intruiging mechanistic hypothesis is forwarded that explains the origin of catalysis and diastereoselectivity.

Authors+Show Affiliations

Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Review

Language

eng

PubMed ID

10891061

Citation

Denmark, S E., and R A. Stavenger. "Asymmetric Catalysis of Aldol Reactions With Chiral Lewis Bases." Accounts of Chemical Research, vol. 33, no. 6, 2000, pp. 432-40.
Denmark SE, Stavenger RA. Asymmetric catalysis of aldol reactions with chiral lewis bases. Acc Chem Res. 2000;33(6):432-40.
Denmark, S. E., & Stavenger, R. A. (2000). Asymmetric catalysis of aldol reactions with chiral lewis bases. Accounts of Chemical Research, 33(6), 432-40.
Denmark SE, Stavenger RA. Asymmetric Catalysis of Aldol Reactions With Chiral Lewis Bases. Acc Chem Res. 2000;33(6):432-40. PubMed PMID: 10891061.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric catalysis of aldol reactions with chiral lewis bases. AU - Denmark,S E, AU - Stavenger,R A, PY - 2000/7/13/pubmed PY - 2000/9/2/medline PY - 2000/7/13/entrez SP - 432 EP - 40 JF - Accounts of chemical research JO - Acc Chem Res VL - 33 IS - 6 N2 - In an extension of studies both on the stereochemical course of the aldol addition and on Lewis-base-catalyzed allylation reactions, we have invented a new Lewis-base-catalyzed asymmetric aldol addition. This Account outlines the conceptual development, the identification of design criteria, and the underlying principles for such a process. The reduction of these elements to practice in the demonstration of enantioselective aldol additions of trichlorosilyl enolates catalyzed by chiral phosphoramides is also presented. From a combination of stereochemical, kinetic, and structural studies, an intruiging mechanistic hypothesis is forwarded that explains the origin of catalysis and diastereoselectivity. SN - 0001-4842 UR - https://www.unboundmedicine.com/medline/citation/10891061/Asymmetric_catalysis_of_aldol_reactions_with_chiral_lewis_bases_ L2 - https://doi.org/10.1021/ar960027g DB - PRIME DP - Unbound Medicine ER -