Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

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20 Citations (Scopus)

Abstract

The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.
Original languageEnglish
Pages (from-to)18944–18948
JournalChemistry - A European Journal
Volume21
Issue number52
Early online date26 Oct 2015
DOIs
Publication statusPublished - 14 Dec 2015

Keywords

  • Organocatalysis
  • Lewis-base
  • N-heterocyclic carbene
  • Pentafluoroethyl
  • Oxetane

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