Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

Org Biomol Chem. 2014 Oct 28;12(40):8072-8. doi: 10.1039/c4ob01358a.

Abstract

The first enantioselective aza-Morita–Baylis–Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent yields with up to 91% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Crystallography, X-Ray
  • Imines / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxindoles
  • Stereoisomerism

Substances

  • 3-amino-2-oxindole
  • Acrylates
  • Imines
  • Indoles
  • Nitriles
  • Oxindoles
  • ketimine