Organocatalytic asymmetric allylic alkylation of oxindoles with Morita-Baylis-Hillman carbonates

Chem Commun (Camb). 2009 Jul 14:(26):3955-7. doi: 10.1039/b905177e. Epub 2009 May 29.

Abstract

The organic Lewis base-catalysed asymmetric allylic alkylation of 3-substituted oxindoles with Morita-Baylis-Hillman carbonates is reported, affording multifunctional oxindoles with adjacent quaternary and tertiary chiral centres (dr up to 92 : 8, 86-97% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Allyl Compounds / chemistry*
  • Carbonates / chemistry*
  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Carbonates
  • Cinchona Alkaloids
  • Indoles
  • Oxindoles
  • 2-oxindole