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N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.

ABSTRACT: N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.

SUBMITTER: Maki BE 

PROVIDER: S-EPMC2657179 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.

Maki Brooks E BE   Scheidt Karl A KA  

Organic letters 20080830 19

N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated  ...[more]

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