Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Jing Cao, Rachel Gillard, Azar Jahanbakhsh, Martin Breugst, David W. Lupton

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Abstract

An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.

Original languageEnglish
Pages (from-to)11791-11796
Number of pages6
JournalACS Catalysis
Volume10
Issue number20
DOIs
Publication statusPublished - 16 Oct 2020

Keywords

  • (3 + 2)-annulation
  • (3 + 3)-annulation
  • (4 + 2) annulation
  • enantioselective catalysis
  • N-heterocyclic carbene
  • α,β-unsaturated acyl azolium

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