Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes |
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Authors: | Chan Audrey Scheidt Karl A |
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Institution: | Department of Chemistry, Northwestern University, Evanston, IL 60208, USA. |
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Abstract: | N-Heterocyclic carbenes derived from benzimidazolium salts are effective catalysts for generating homoenolate species from alpha,beta-unsaturated aldehydes. These nucleophilic intermediates can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile, thereby promoting a highly efficient conversion of an alpha,beta-unsaturated aldehyde into a saturated ester. A kinetic resolution of secondary alcohols can be achieved using chiral imidazoylidene catalysts. reaction: see text] |
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