Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis

Alyn T. Davies, Philip M. Pickett, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)
3 Downloads (Pure)

Abstract

The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into δ-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.

Original languageEnglish
Pages (from-to)2696-2700
Number of pages5
JournalACS Catalysis
Volume4
Issue number8
Early online date15 Jul 2014
DOIs
Publication statusPublished - Aug 2014

Keywords

  • Asymmetric organocatalysis
  • N-heterocyclic carbenes
  • Cycloaddition
  • Trifluoromethyl
  • Dihydropyranones
  • Delta-lactones
  • Diels-alder reactions
  • One-pot synthesis
  • Enantioselective synthesis
  • Fused dihydropyranones
  • Medicinal chemistry
  • 4+2 Cycloaddition
  • Aldehydes
  • Ketenes
  • Functionalization

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