Gold(I)-catalyzed tandem cyclization-selective migration reaction of 1,3-dien-5-ynes: regioselective synthesis of highly substituted benzenes

Org Lett. 2011 Sep 16;13(18):4970-3. doi: 10.1021/ol202129n. Epub 2011 Aug 25.

Abstract

Highly substituted benzene derivatives have been easily prepared in a regioselective way from readily available 1,3-hexadien-5-ynes through a gold(I)-catalyzed tandem reaction. The process involves an initial cyclization followed by a selective Wagner-Meerwein shift in which the migration preference seems to be determined by the ability to stabilize a positive charge.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Molecular Structure
  • Organogold Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Benzene Derivatives
  • Organogold Compounds
  • Gold