Catalytic Enantioselective Decarboxylative Protonation

Justin T. Mohr, Toyoki Nishimata, Douglas C. Behenna and Brian M. Stoltz*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, Email: stoltzcaltech.edu

J. T. Mohr, T. Nishimata, D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc., 2006, 128, 11348-11349.

DOI: 10.1021/ja063335a

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Abstract

A highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters adjacent to cyclic ketones relies on catalytic decarboxylative protonation of readily accessible racemic quaternary β-ketoesters.

see article for more examples

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Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles

C. M. Reeves, D. C. Behenna, B. M. Stoltz, Org. Lett., 2014, 16, 2314-2317.

Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters

J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. Int. Ed., 2005, 44, 6924-6927.

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Key Words

decarboxylation, asymmetric catalysis, enolates, palladium

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ID: J48-Y2006-2840