A simple and versatile re-catalyzed Meyer-Schuster rearrangement of propargylic alcohols to alpha,beta-unsaturated carbonyl compounds

Chemistry. 2009;15(16):3940-4. doi: 10.1002/chem.200802622.

Abstract

Rhenium does the job! A readily available rhenium complex efficiently catalyzed the direct Meyer-Schuster-like rearrangement of different alkyl- and aryl-substituted propargylic secondary and tertiary alcohols to the corresponding alpha,beta-unsaturated compounds, which were produced with virtually complete E stereoselectivity. The reaction proceeded under neutral conditions and no racemization of potentially enolizable stereocenters was observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Ketones
  • Propanols
  • propargyl alcohol