Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

Brooks E. Maki, Audrey Chan, Eric M. Phillips, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

207 Scopus citations

Abstract

(Chemical Equation Presented) N-Heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. A variety of ester derivatives can be synthesized, including protected carboxylates. This one-pot tandem oxidation represents the first organocatalytic oxidation of alcohols to esters. Saturated esters can also be accessed from aldehydes using this method. Through the utilization of a chiral catalyst, the acyl-heteroazolium intermediate becomes a chiral acylating agent, which can desymmetrize meso-1,2-diols.

Original languageEnglish (US)
Pages (from-to)371-374
Number of pages4
JournalOrganic Letters
Volume9
Issue number2
DOIs
StatePublished - Jan 18 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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