Construction of quaternary stereogenic carbon centers by the Lewis base catalyzed conjugate addition of silyl ketene imines to α,β- unsaturated aldehydes and ketones

Scott E Denmark, Tyler W. Wilson

Research output: Contribution to journalArticle

Abstract

Highly site-selective Mukaiyama-Michael additions of silyl ketene imines to α,β-unsaturated aldehydes and ketones are described. The combination of silicon tetrachloride and a chiral bisphosphoramide provides an effective catalyst system for promoting the addition of silyl ketene imines to a variety of aromatic enals with high site selectivity and moderate to good diastereo- and enantioselectivity.

Original languageEnglish (US)
Pages (from-to)1723-1728
Number of pages6
JournalSynlett
Issue number11
DOIs
StatePublished - Jun 29 2010

Keywords

  • Lewis base
  • Michael addition
  • aldehydes
  • asymmetric catalysis
  • quaternary carbon

ASJC Scopus subject areas

  • Organic Chemistry

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