Synthesis of highly functionalized chiral 3,3'-disubstituted oxindoles via an organocatalytic enantioselective Michael addition of nitroalkanes to indolylidenecyanoacetates

Org Lett. 2012 Jan 6;14(1):134-7. doi: 10.1021/ol202931e. Epub 2011 Dec 12.

Abstract

An efficient bifunctional cinchona alkaloid derived thiourea-promoted enantioselective conjugate addition of nitroalkanes to indolylidenecyanoacetates has been developed under neat conditions. The process leads to synthetically interesting densely functionalized 3,3'-disubstituted oxindoles with creation of up to three stereogenic centers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Alkanes / chemistry*
  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Nitrogen / chemistry*
  • Oxindoles
  • Stereoisomerism

Substances

  • Acetates
  • Alkanes
  • Indoles
  • Oxindoles
  • 2-oxindole
  • indole
  • Nitrogen
  • cyanoacetic acid