Copper(I) thiolate catalysts in asymmetric conjugate addition reactions

Org Lett. 2004 Jun 10;6(12):1959-62. doi: 10.1021/ol049457u.

Abstract

[structure: see text] Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R(2)Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis
  • Catalysis
  • Ketones / chemical synthesis
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Zinc Compounds / chemical synthesis*

Substances

  • Alcohols
  • Ketones
  • Organometallic Compounds
  • Zinc Compounds
  • copper(I)-thiolate