Enantioselective tandem reaction of chromone-derived Morita-Baylis-Hillman carbonates with benzylamines catalyzed by a trifunctional organocatalyst: the synthesis of chiral 3-aminomethylene-flavanones

Chem Commun (Camb). 2013 May 7;49(35):3697-9. doi: 10.1039/c3cc41011k. Epub 2013 Mar 27.

Abstract

An enantioselective tandem reaction of chromones-derived MBH carbonates (1) with benzylamines (2) catalyzed by a trifunctional organocatalyst, cinchonidine-amide-thiourea, has been developed in moderate to good yields (50-87%) and enantioselectivities (up to 89% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Benzylamines / chemistry*
  • Carbonates / chemistry*
  • Catalysis
  • Chromones / chemistry
  • Cinchona Alkaloids / chemistry
  • Flavanones / chemical synthesis*
  • Stereoisomerism
  • Thiourea / chemistry

Substances

  • Amides
  • Benzylamines
  • Carbonates
  • Chromones
  • Cinchona Alkaloids
  • Flavanones
  • cinchonidine
  • Thiourea