Enantioselective organocatalytic Michael-hemiketalization catalyzed by a trans-bifunctional indane thiourea catalyst

Org Biomol Chem. 2011 May 21;9(10):3691-7. doi: 10.1039/c1ob05404j. Epub 2011 Apr 11.

Abstract

An efficient, convenient and enantioselective Michael-hemiketalization reaction has been developed for the synthesis of naphthoquinones. In this work, a novel trans-bifunctional indane thiourea catalyst has been reported to promote this process to afford high yields (up to 99%) and high to excellent enantiomeric excesses (90-98% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogen Bonding
  • Ketones / chemistry*
  • Naphthoquinones / chemistry
  • Stereoisomerism
  • Substrate Specificity
  • Thiourea / chemistry*

Substances

  • Ketones
  • Naphthoquinones
  • Thiourea