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, Email: scheidtnorthwestern.edu

B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett., 2007, 9, 371-374.

DOI: 10.1021/ol062940f

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Abstract

N-Heterocyclic carbenes catalyze the oxidation of various allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. Saturated esters can also be accessed from aldehydes using this method. A desymmetration of meso-1,2-diols using a chiral catalyst is described.

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proposed mechanism

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N-Heterocyclic Carbene-Catalyzed Oxidation of Unactivated Aldehydes to Esters

B. E. Marki, K. A. Scheidt, Org. Lett., 2008, 10, 4331-4334.

Key Words

Esters, Oxidative Esterification, Manganese(IV) Oxide, Organocatalysis

ID: J54-Y2007-0270