An efficient organocatalytic enantioselective Michael addition of aryl methyl ketones with 2-furanones: highly functionalized chiral 3,4-substituted lactones

Chem Commun (Camb). 2013 Feb 14;49(13):1333-5. doi: 10.1039/c2cc35488h. Epub 2013 Jan 10.

Abstract

The efficient asymmetric Michael addition reactions of aryl methyl ketones with 2-furanones were catalyzed by a simple and commercially available chiral 1,2-diphenyl-1,2-ethanediamine and p-TSA·H(2)O as cocatalyst with good yields (up to 95%) and excellent enantioselectivities (up to >99% ee). A bi-functional catalytic mechanism for the reaction was proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Furans / chemistry*
  • Ketones / chemistry*
  • Lactones / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Furans
  • Ketones
  • Lactones