N-Heterocyclic carbene-catalyzed oxidations |
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Authors: | Brooks E Maki |
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Institution: | Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, United States |
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Abstract: | N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols. |
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