Asymmetric catalysis of aldol reactions with chiral Lewis bases

Scott E Denmark, Robert A. Stavenger

Research output: Contribution to journalArticle

Abstract

In an expression 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 fowarded that explain the origin of catalysis and diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)432-440
Number of pages9
JournalAccounts of chemical research
Volume33
Issue number6
DOIs
StatePublished - Jul 19 2000

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Lewis Bases
Catalysis
Phosphoramides
Allylation
Demonstrations
Kinetics
3-hydroxybutanal

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Asymmetric catalysis of aldol reactions with chiral Lewis bases. / Denmark, Scott E; Stavenger, Robert A.

In: Accounts of chemical research, Vol. 33, No. 6, 19.07.2000, p. 432-440.

Research output: Contribution to journalArticle

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