Protonation of homoenolate equivalents generated by N-heterocyclic carbenes

Brooks E. Maki, Audrey Chan, Karl A Scheidt

Research output: Contribution to journalReview articlepeer-review

72 Scopus citations

Abstract

Homoenolate equivalents are generated by Lewis basic N-heterocyclic carbene catalysts and then protonated to generate efficiently saturated esters from unsaturated aldehydes. This reactivity is extended to the generation of β-acylvinyl anions from alkynyl aldehydes. The asymmetric protonation of a homoenolate equivalent generated from a β,β-disubstituted aldehyde can be accomplished with a chiral N-heterocyclic carbene.

Original languageEnglish (US)
Pages (from-to)1306-1315
Number of pages10
JournalSynthesis
Issue number8
DOIs
StatePublished - Apr 17 2008

Keywords

  • Asymmetric catalysis
  • Carbenes
  • Esters
  • Protonations
  • Umpolung

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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