Highly enantioselective Michael addition of 3-arylthio- and 3-alkylthiooxindoles to nitroolefins catalyzed by a simple cinchona alkaloid derived phosphoramide

Chem Commun (Camb). 2014 Dec 14;50(96):15179-82. doi: 10.1039/c4cc06417h.

Abstract

A new cinchona alkaloid derived bifunctional tertiary amine-phosphoramide is identified as a highly enantioselective catalyst for Michael addition of both unprotected 3-arylthio- and 3-alkylthiooxindoles to nitroolefins. The phosphoramide moiety of plays an indispensable role in this reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Indoles / chemistry*
  • Phosphoramides / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alkenes
  • Cinchona Alkaloids
  • Indoles
  • Phosphoramides
  • Sulfhydryl Compounds
  • phosphoramide