Diastereoselective aldol addition reactions of a chiral methyl ketone trichlorosilyl enolate under lewis base catalysis

S. E. Denmark, S. Fujimori

Research output: Contribution to journalArticle

Abstract

The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.

Original languageEnglish (US)
Pages (from-to)1024-1029
Number of pages6
JournalSynlett
Issue numberSPEC. ISS
DOIs
StatePublished - 2001

Keywords

  • Aldol addition
  • Diastereoselection
  • Lewis base catalysis
  • Trichlorosilyl enolate

ASJC Scopus subject areas

  • Organic Chemistry

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