Catalytic enantioselective desymmetrization of meso-glutaric anhydrides using a stable Ni2-Schiff base catalyst

Org Lett. 2012 Mar 2;14(5):1358-61. doi: 10.1021/ol3002078. Epub 2012 Feb 16.

Abstract

We describe the desymmetrization of meso-glutaric anhydrides to chiral hemiesters using a bench-stable homodinuclear Ni(2)-(Schiff base) complex as the catalyst in good to excellent yield (up to 99%) and enantioselectivity (up to 94%). Using the opposite enantiomer of the catalyst, we obtained the same yield and enantioselectivity with the opposite configuration, thereby gaining access to both hemiester enantiomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anhydrides / chemistry*
  • Catalysis
  • Glutarates / chemistry*
  • Molecular Structure
  • Nickel / chemistry*
  • Schiff Bases / chemistry
  • Stereoisomerism

Substances

  • Anhydrides
  • Glutarates
  • Schiff Bases
  • glutaric anhydride
  • Nickel