A facile method for the synthesis of oxindole based quaternary alpha-aminonitriles via the Strecker reaction

Org Biomol Chem. 2010 Sep 7;8(17):3847-50. doi: 10.1039/c0ob00174k. Epub 2010 Jul 8.

Abstract

The direct alpha-cyanoamination of isatins using TMSCN has been developed, which is carried out in methanol without any catalyst. A new bifunctional cinchona alkaloid-based phosphinamide catalyst 7 could promote the Strecker reaction of isatins derived ketimine with TMSCN in up to 74% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Indoles / chemical synthesis*
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxindoles
  • Stereoisomerism

Substances

  • Amines
  • Indoles
  • Nitriles
  • Oxindoles
  • 2-oxindole