Regiospecific organocatalytic asymmetric aldol reaction of methyl ketones and alpha,beta-unsaturated trifluoromethyl ketones

Org Lett. 2007 Mar 29;9(7):1343-5. doi: 10.1021/ol070217z. Epub 2007 Mar 10.

Abstract

[structure: see text]. The aldol reaction of methyl ketones and alpha,beta-unsaturated trifluoromethyl ketones occurred under mild conditions with the combination of proline-derived N-sulfonylamide and trifluoroacetic acid as the catalyst to give the corresponding unsaturated alpha-trifluoromethyl tertiary alcohols in high yields with good enatioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetone / chemistry
  • Aldehydes / chemistry*
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Proline / chemistry
  • Stereoisomerism
  • Sulfur Compounds / chemistry
  • Trifluoroacetic Acid / chemistry

Substances

  • Aldehydes
  • Hydrocarbons, Fluorinated
  • Ketones
  • Sulfur Compounds
  • Acetone
  • 3-hydroxybutanal
  • Proline
  • Trifluoroacetic Acid