Three-component synthesis of polysubstituted pyrroles from α-diazoketones, nitroalkenes, and amines

Org Lett. 2011 Sep 2;13(17):4668-71. doi: 10.1021/ol201891r. Epub 2011 Aug 10.

Abstract

Polysubstituted pyrroles are regiospecifically synthesized via the copper-catalyzed three-component reaction of α-diazoketones, nitroalkenes, and amines under aerobic conditions. The cascade process involves an N-H insertion of carbene, a copper-catalyzed oxidative dehydrogenation of amine, and a [3 + 2] cycloaddition of azomethine ylide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amines / chemistry*
  • Crystallography, X-Ray
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Amines
  • Ketones
  • Nitro Compounds
  • Pyrroles