Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium

Rachel M. Gillard, Jared E.M. Fernando, David W. Lupton

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22 Citations (Scopus)

Abstract

Herein we report the enantioselective N-heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio- and diastereo-enriched cyclohexenes (most >97:3 er and >20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6-addition/β-lactonization.

Original languageEnglish
Pages (from-to)4712-4716
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number17
DOIs
Publication statusPublished - 16 Apr 2018

Keywords

  • 1,6-addition
  • dienyl acyl azolium
  • enantioselective catalysis
  • N-heterocyclic carbene
  • β-lactonization

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