Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes
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- 20 December 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (2) , 371-374
- https://doi.org/10.1021/ol062940f
Abstract
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.Keywords
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