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Published October 28, 2005 | public
Journal Article

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


Stereochemical alchemy! Racemic allyl β-ketoesters allow the regiocontrolled formation of enolates, where the same catalyst is intimately involved in both the stereoablative (C-C bond-breaking) and stereoselective (C-C bond-forming) steps. This mechanistic and practical insight led to the formation of multiple quaternary carbon stereocenters in a single cascade reaction (see scheme).

Additional Information

© 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: June 11, 2005; Published online: October 5, 2005. The authors wish to thank the Fannie and John Hertz Foundation (predoctoral fellowship to D.C.B.), the NIH (postdoctoral fellowship to A.M.H.), Research Corporation, the Camille and Henry Dreyfus Foundation, Merck, Pfizer, and Lilly for financial support, and Prof. D. A. Dougherty for helpful discussions.

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August 22, 2023
October 24, 2023