Conversion of α,β-unsaturated aldehydes into saturated esters: An umpolung reaction catalyzed by nucleophilic carbenes

Audrey Chan, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

311 Scopus citations

Abstract

(Chemical Equation Presented) N-Heterocyclic carbenes derived from benzimidazolium salts are effective catalysts for generating homoenolate species from α,β-unsaturated aldehydes. These nucleophilic intermediates can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile, thereby promoting a highly efficient conversion of an α,β-unsaturated aldehyde into a saturated ester. A kinetic resolution of secondary alcohols can be achieved using chiral imidazoylidene catalysts.

Original languageEnglish (US)
Pages (from-to)905-908
Number of pages4
JournalOrganic Letters
Volume7
Issue number5
DOIs
StatePublished - Mar 3 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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