Oxidative rearrangement of tertiary allylic alcohols employing oxoammonium salts

J Org Chem. 2008 Jun 20;73(12):4750-2. doi: 10.1021/jo800634r. Epub 2008 May 24.

Abstract

Practical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to beta-substituted alpha,beta-unsaturated carbonyl compounds employing oxoammonium salts are described. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. The counteranion of the oxoammonium salt plays crucial roles on this oxidative rearrangement.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Oxidation-Reduction
  • Propanols / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Salts / chemistry*
  • Spectrophotometry, Infrared

Substances

  • Propanols
  • Quaternary Ammonium Compounds
  • Salts
  • allyl alcohol