Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes

Brooks E. Maki, Audrey Chan, Eric M. Phillips, and Karl A. Scheidt*
Department of Chemistry, Northwestern University, Evanston, Illinois 60208
Org. Lett., 2007, 9 (2), pp 371–374
DOI: 10.1021/ol062940f
Publication Date (Web): December 20, 2006
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, scheidt@northwestern.edu

Abstract

Abstract Image

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.

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History

  • Published In Issue January 18, 2007
  • Received December 4, 2006

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