Stereoselective Barbier-type allylation reaction of trifluoromethyl aldimines

J Org Chem. 2003 Aug 8;68(16):6444-6. doi: 10.1021/jo034205c.

Abstract

Trifluoromethyl aldimines could react, under Barbier conditions in the presence of activated zinc, in DMF at room temperature or in THF at reflux, with various allyl bromides to provide the corresponding homoallylamines. Secondary homoallyl trifluoromethylamines were stereoselectively obtained from the optically active aldimine 12 with an excellent diastereoisomeric excess (98%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemical synthesis
  • Imines / chemistry*
  • Indicators and Reagents
  • Indium / chemistry
  • Magnesium / chemistry
  • Stereoisomerism
  • Zinc / chemistry

Substances

  • Allyl Compounds
  • Imines
  • Indicators and Reagents
  • Indium
  • Magnesium
  • Zinc