Highly enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones

Org Biomol Chem. 2008 Jan 21;6(2):349-53. doi: 10.1039/b713129a. Epub 2007 Dec 3.

Abstract

The highly enantioselective Michael addition of malononitrile to acyclic and cyclic alpha,beta-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83-97% ee).

MeSH terms

  • Amines / chemistry
  • Catalysis
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Conformation
  • Nitriles / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Ketones
  • Nitriles
  • dicyanmethane