Asymmetric direct α-alkylation of 2-oxindoles with Michler's hydrol catalyzed by bis-cinchona alkaloid-Brønsted acid via an SN1-type pathway

Chem Commun (Camb). 2013 Feb 25;49(16):1636-8. doi: 10.1039/c3cc39012h.

Abstract

An enantioselective direct α-alkylation of 2-oxindoles with Michler's hydrol via an S(N)1-type pathway in the non-covalent activation mode using the bis-cinchona alkaloid and Brønsted acid as a co-catalyst was developed and good to high yields and enantioselectivities were obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Alkylation
  • Aniline Compounds / chemistry*
  • Benzhydryl Compounds / chemistry*
  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Stereoisomerism

Substances

  • Acids
  • Aniline Compounds
  • Benzhydryl Compounds
  • Cinchona Alkaloids
  • Indoles
  • Michler's hydrol blue
  • Oxindoles
  • 2-oxindole