Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine

Org Lett. 2014 Sep 5;16(17):4626-9. doi: 10.1021/ol5022178. Epub 2014 Aug 21.

Abstract

The first effective example of asymmetric conjugate addition-protonation reactions of thiols to α-substituted vinyl ketones by chiral primary amine catalysis is reported. A simple chiral primary-tertiary diamine catalyst derived from l-phenylalanine was found to promote the sulfa-Michael addition-protonation reactions with good to excellent enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Diamines / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Phenylalanine / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Amines
  • Diamines
  • Ketones
  • Sulfhydryl Compounds
  • Vinyl Compounds
  • Phenylalanine