Enantioselective N-Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Jared E.M. Fernando, Yuji Nakano, Changhe Zhang, David W. Lupton

Research output: Contribution to journalArticleResearchpeer-review

18 Citations (Scopus)

Abstract

The catalytic umpolung of imines remains an underdeveloped approach to reaction discovery. Herein we report an enantioselective aza-Stetter reaction that proceeds via imine umpolung using N-heterocyclic carbene catalysis. The reaction proceeds with high levels of enantioselectivity (all ≥96:4 er) and good generality (21 examples). Mechanistic studies are reported and are consistent with turnover-limiting addition of the NHC to the imine.

Original languageEnglish
Pages (from-to)4007-4011
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number12
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • enantioselective catalysis
  • imine umpolung
  • N-heterocyclic carbenes
  • Stetter reaction

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