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

Authors

  • Justin T. Mohr,

    1. The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • Douglas C. Behenna,

    1. The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • Andrew M. Harned Dr.,

    1. The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • Brian M. Stoltz Prof.

    1. The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA, Fax: (+1) 626-564-9297
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  • 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.

Abstract

original image

Stereochemische Alchemie! Aus racemischen Allyl-β-ketoestern lassen sich regiokontrolliert Enolate erzeugen, wobei derselbe Katalysator sowohl den Abbau (C-C-Bindungsbruch) als auch den selektiven Aufbau eines Stereozentrums (C-C-Verknüpfung) vermittelt. Auf diese Art wurden mehrere quartäre Kohlenstoffstereozentren in einer einzigen Kaskadenreaktion gebildet (siehe Schema).

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