Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary amine thiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters

Org Biomol Chem. 2012 Jan 14;10(2):236-9. doi: 10.1039/c1ob06413d. Epub 2011 Oct 21.

Abstract

Chiral bifunctional tertiary amine thiourea was applied to catalyze the asymmetric hydroxyamination of 3-subsituted oxindoles with nitrosobenzene to construct 3-amino-2-oxindoles with quaternary stereocenters in good yields (up to 91%) and enantioselectivities (up to 90% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Amines / chemistry*
  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • 3-amino-2-oxindole
  • Amines
  • Indoles
  • Oxindoles
  • 2-oxindole
  • Thiourea