Enantioselective (4+2) annulation of donor–acceptor cyclobutanes by N-heterocyclic carbene catalysis

Alison Levens, Adam Ametovski, David Lupton

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30 Citations (Scopus)

Abstract

Herein we report the enantioselective (4+2) annulation of donor–acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.

Original languageEnglish
Pages (from-to)16136-16140
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number52
DOIs
Publication statusPublished - 23 Dec 2016

Keywords

  • cyclohexanes
  • donor–acceptor cyclobutanes
  • enantioselective catalysis
  • N-heterocyclic carbenes
  • organocatalysis

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