Lewis base activation of Lewis acids: Vinylogous aldol additions of silyl dienol ethers to aldehydes

Scott E Denmark, John R. Heemstra

Research output: Contribution to journalArticle

Abstract

Highly regioselective vinylogous aldol additions of silyl dienol ethers derived from simple α,β-unsaturated ketones are described. The catalyst system of silicon tetrachloride activated by chiral bisphosphoramide (R,R)-1 effectively promotes the addition of both γ-substituted and unsubstituted silyl dienol ethers to a variety of aldehydes with exclusive γ-regioselectivity and good to excellent diastereo- and enantioselectivity.

Original languageEnglish (US)
Pages (from-to)2411-2416
Number of pages6
JournalSynlett
Issue number13
DOIs
StatePublished - Nov 3 2004

Keywords

  • Asymmetric catalysis
  • Ketones
  • Lewis base
  • Regioselectivity
  • Vinylogous aldol reactions

ASJC Scopus subject areas

  • Organic Chemistry

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