Catalytic, enantioselective, vinylogous aldol reactions

Scott E. Denmark, John R. Heemstra, Gregory L. Beutner

Research output: Contribution to journalReview article

Abstract

In 1935, R. C. Fuson formulated the principle of vinylogy to explain how the influence of a functional group may be felt at a distant point in the molecule when this position is connected by conjugated double-bond linkages to the group. In polar reactions, this concept allows the extension of the electrophilic or nucleophilic character of a functional group through the π system of a carbon-carbon double bond. This vinylogous extension has been applied to the aldol reaction by employing "extended" dienol ethers derived from γ-enolizable a,β-unsaturated carbonyl compounds. Since 1994, several methods for the catalytic, enantioselective, vinylogous aldol reaction have appeared, with which varying degrees of regio- (site), enantio-, and diastereoselectivity can be attained. In this Review, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed.

Original languageEnglish (US)
Pages (from-to)4682-4698
Number of pages17
JournalAngewandte Chemie - International Edition
Volume44
Issue number30
DOIs
StatePublished - Jul 25 2005

Keywords

  • Aldol reactions
  • Asymmetric catalysis
  • Dienol ethers
  • Regioselectivity
  • Vinylogy

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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