Deracemization of Quaternary Stereocenters by Pd-Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β-Ketoesters†
Justin T. Mohr
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
Search for more papers by this authorDouglas C. Behenna
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
Search for more papers by this authorAndrew M. Harned Dr.
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
Search for more papers by this authorBrian M. Stoltz Prof.
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
Search for more papers by this authorJustin T. Mohr
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
Search for more papers by this authorDouglas C. Behenna
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
Search for more papers by this authorAndrew M. Harned Dr.
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
Search for more papers by this authorBrian M. Stoltz Prof.
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
Search for more papers by this authorThe 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.
Graphical Abstract
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).
Supporting Information
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References
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