Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones

Org Lett. 2007 Aug 30;9(18):3707-10. doi: 10.1021/ol701791r. Epub 2007 Aug 10.

Abstract

The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry, Pharmaceutical
  • Cinchona Alkaloids / chemistry*
  • Ketones / chemistry*
  • Methylation
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Cinchona Alkaloids
  • Ketones
  • Quaternary Ammonium Compounds
  • tetramethylammonium