A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

Eric M. Phillips*, Manabu Wadamoto, Audrey Chan, Karl A. Scheidt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

176 Scopus citations

Abstract

(Chemical Equation Presented) Metal-less Michael: A highly diastereo-and enantioselective intramolecular Michael addition of α,β-unsaturated aldehydes to enones catalyzed by an N-heterocyclic carbene (NHC) has been developed. The reaction is tolerant of alkyl and aromatic substituents, as well as saturated and unsaturated tethers between the enal and conjugate acceptor (see scheme).

Original languageEnglish (US)
Pages (from-to)3107-3110
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number17
DOIs
StatePublished - 2007

Keywords

  • Acylation
  • Asymmetric catalysis
  • Michael addition
  • N-heterocyclic carbenes
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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