Cu(OTf)2-catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with arylidene malonates using bis(sulfonamide)-diamine ligands

J Org Chem. 2013 Jun 7;78(11):5611-7. doi: 10.1021/jo400747d. Epub 2013 May 13.

Abstract

A highly efficient Cu-catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with arylidene malonates using simple, stable, and easily prepared bis-sulfonamide diamine ligands was developed. The desired products were obtained in up to 99% yield with 96% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Diamines / chemical synthesis*
  • Diamines / chemistry
  • Indoles / chemistry*
  • Ligands
  • Malonates / chemistry*
  • Mesylates / chemistry*
  • Molecular Structure
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry

Substances

  • Diamines
  • Indoles
  • Ligands
  • Malonates
  • Mesylates
  • Sulfonamides
  • trifluoromethanesulfonic acid