Remote activation of the nucleophilicity of isatin

Org Lett. 2014 Mar 21;16(6):1740-3. doi: 10.1021/ol500421k. Epub 2014 Mar 10.

Abstract

The concept of the remote activation of reactivity was first applied in asymmetric organocatalysis. An isatin 3-phenylimine derivative acts as a donor in the thiourea catalyzed asymmetric addition to unsaturated 1,4-ketoesters, affording aza-Michael adducts in high enantiomeric purity and yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Esters
  • Imines / chemistry
  • Isatin / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Thiourea / chemistry

Substances

  • Esters
  • Imines
  • Isatin
  • Thiourea