Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes

Chem Commun (Camb). 2009 Dec 7:(45):6988-90. doi: 10.1039/b913554e. Epub 2009 Oct 14.

Abstract

The enantioselective asymmetric gold-catalyzed cycloisomerization reactions of heteroatom tethered 1,6-enynes are conducted in the presence of a chiral cationic Au(i) catalyst ((R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2)/AgOTf system) in toluene under mild conditions and lead to functionalized bicyclo[4.1.0]heptene derivatives in excellent enantiomeric excesses ranging from 90-98%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Stereoisomerism
  • Toluene / chemistry

Substances

  • Bridged Bicyclo Compounds
  • Toluene
  • Gold