Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes
Audrey Chan and Karl A. Scheidt*
*Department of Chemistry, Northwestern University, Evanston, Illinois 60208,
Email: scheidt
northwestern.edu
A. Chan, K. A. Scheidt, Org. Lett., 2005, 7, 905-908.
DOI: 10.1021/ol050100f (free Supporting Information)
Abstract
N-Heterocyclic carbenes are effective catalysts for an Umpolung reaction of α,β-unsaturated aldehydes. The generated homoenolate species can be protonated, and the resulting activated carbonyl unit is trapped with an alcohol nucleophile to form a saturated ester.
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Key Words
Umpolung, Redox Esterification, Organocatalysis
ID: J54-Y2005-230
