Copper-catalyzed enantioselective conjugate addition of grignard reagents to methyl 4,4,4-trifluorocrotonate: synthesis of enantioenriched trifluoromethylated compounds

Chem Asian J. 2015 Apr;10(4):844-8. doi: 10.1002/asia.201403303. Epub 2015 Feb 5.

Abstract

Copper-catalyzed enantioselective 1,4-conjugate addition of methyl 4,4,4-trifluorocrotonate with aliphatic Grignard reagents to access an asymmetric tertiary carbon center attached with a trifluoromethyl group was achieved under mild reaction conditions. The desired products could be obtained in reasonable yields and good enantioselectivities.

Keywords: 1,4-conjugate addition; 4,4,4-trifluorocrotonate; aliphatic Grignard reagents; copper catalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Crotonates / chemistry*
  • Halogenation
  • Hydrocarbons, Fluorinated / chemistry*
  • Methylation
  • Models, Molecular
  • Molecular Structure
  • Pharmaceutical Preparations / chemical synthesis
  • Pharmaceutical Preparations / chemistry*

Substances

  • Crotonates
  • Hydrocarbons, Fluorinated
  • Pharmaceutical Preparations
  • methyl 4,4,4-trifluorocrotonate
  • Copper