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
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.
see article for more examples
Enantioselective β-Protonation by a Cooperative Catalysis Strategy
M. H. Wang, D. T. Cohen, C. Benjamin Schwamb, R. K. Mishra, K. A. Scheidt, J. Am. Chem. Soc., 2015, 137, 5891-5894.
Key Words
Umpolung, Redox Esterification, Organocatalysis
ID: J54-Y2005-230
