Enantioselective β-Protonation by a Cooperative Catalysis Strategy

Michael H. Wang, Daniel T. Cohen, C. Benjamin Schwamb, Rama K. Mishra and Karl A. Scheidt*

*Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Silverman Hall, Evanston, Illinois 60208, United States, Email: scheidtnorthwestern.edu

M. H. Wang, D. T. Cohen, C. Benjamin Schwamb, R. K. Mishra, K. A. Scheidt, J. Am. Chem. Soc., 2015, 137, 5891-5894.

DOI: 10.1021/jacs.5b02887

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Abstract

A cooperative catalyst system enhances both yield and selectivity of an enantioselective N-heterocyclic carbene (NHC)-catalyzed β-protonation providing a broad range of aryl-oxobutenoates and highly enantioenriched succinate derivatives. The method demonstrates the benefits of combining different activation modes in organocatalysis.

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Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes

A. Chan, K. A. Scheidt, Org. Lett., 2005, 7, 905-908.

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Key Words

redox esterification, β-arylated esters, organocatalysis

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ID: J48-Y2015