Cooperative dual catalysis: application to the highly enantioselective conjugate cyanation of unsaturated imides

J Am Chem Soc. 2004 Aug 18;126(32):9928-9. doi: 10.1021/ja046653n.

Abstract

Cooperative heterobimetallic catalysis was used as a design principle to achieve a highly reactive system for the enantioselective conjugate addition of cyanide to alpha,beta-unsaturated imides. A dual-catalyst pathway involving chiral (salen)Al complex 1b and chiral (pybox)Er complex 4b provides measurable improvements in rates and enantioselectivities relative to single-catalyst systems. Mechanistic studies point to a cooperative bimetallic mechanism involving activation of the imide by the Al complex and activation of cyanide by the Er complex.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aluminum Chloride
  • Aluminum Compounds / chemistry
  • Catalysis
  • Chlorides / chemistry
  • Ethylenediamines / chemistry
  • Hydrogen Cyanide / chemistry*
  • Imides / chemistry*
  • Lanthanoid Series Elements / chemistry
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Aluminum Compounds
  • Chlorides
  • Ethylenediamines
  • Imides
  • Lanthanoid Series Elements
  • Organometallic Compounds
  • Hydrogen Cyanide
  • Aluminum Chloride
  • disalicylaldehyde ethylenediamine