Asymmetric Catalysis of Aldol Reactions with Chiral Lewis Bases

  • Denmark S
  • Stavenger R
  • 6

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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.

Author-supplied keywords

  • Aldehydes
  • Aldehydes: chemistry
  • Catalysis
  • Ketones
  • Ketones: chemistry
  • Molecular Conformation
  • Organometallic Compounds
  • Organometallic Compounds: chemistry
  • Organophosphorus Compounds
  • Organophosphorus Compounds: chemistry
  • Silanes
  • Stereoisomerism

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Authors

  • S E Denmark

  • R a Stavenger

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