Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones

Org Lett. 2007 Feb 1;9(3):413-5. doi: 10.1021/ol062718a.

Abstract

[reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amines / chemistry
  • Anticoagulants / chemical synthesis*
  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Models, Chemical
  • Models, Molecular
  • Quinine / chemistry
  • Solvents / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amines
  • Anticoagulants
  • Ketones
  • Solvents
  • Quinine