Enantioselective organocatalytic michael addition of malonates to alpha,beta-unsaturated ketones

Org Lett. 2009 Feb 5;11(3):753-6. doi: 10.1021/ol802892h.

Abstract

A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and acyclic enones could react very well with different malonates in the presence of 4 with 0.5-10 mol % catalyst loading affording chiral Michael adducts with excellent yields and ee values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cinchona Alkaloids / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Malonates / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cinchona Alkaloids
  • Ketones
  • Malonates