Gold(I)/(III)-catalyzed rearrangement of divinyl ketones and acyloxyalkynyloxiranes into cyclopentenones

Org Lett. 2014 Feb 7;16(3):908-11. doi: 10.1021/ol403663j. Epub 2014 Jan 23.

Abstract

Multifaceted gold(I/III) catalysts with their carbophilic and oxophilic characters catalyzed very efficiently the formation of hydroxylated cyclopentenones from simple divinyl ketones or acyloxyalkynyloxiranes. The Nazarov reaction is rapidly performed in dichloroethane with 5 mol % of the simple gold(III) trichloride salt at 70 °C, while the rearrangement of alkynyloxiranes requires 5 mol % of a more stable NHC gold(III) triflimidate complex.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Epoxy Compounds / chemistry*
  • Gold / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Cyclopentanes
  • Epoxy Compounds
  • Ketones
  • Vinyl Compounds
  • Gold
  • cyclopentenone