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Catalytic Enantioselective Stereoablative Alkylation of 3-Halooxindoles: Facile Access to Oxindoles with C3 All-Carbon Quaternary Stereocenters

Authors

  • Sandy Ma,

    1. Division of Chemistry and Chemical Engineering and the Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125 (USA)
    2. Department of Molecular Medicine, Beckman Research Institute at City of Hope, Duarte, CA 91001 (USA), Fax: (+1) 626-564-9297
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  • Xiaoqing Han Dr.,

    1. Division of Chemistry and Chemical Engineering and the Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125 (USA)
    2. Department of Molecular Medicine, Beckman Research Institute at City of Hope, Duarte, CA 91001 (USA), Fax: (+1) 626-564-9297
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  • Shyam Krishnan Dr.,

    1. Division of Chemistry and Chemical Engineering and the Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125 (USA)
    2. Department of Molecular Medicine, Beckman Research Institute at City of Hope, Duarte, CA 91001 (USA), Fax: (+1) 626-564-9297
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  • Scott C. Virgil Dr.,

    1. Division of Chemistry and Chemical Engineering and the Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125 (USA)
    2. Department of Molecular Medicine, Beckman Research Institute at City of Hope, Duarte, CA 91001 (USA), Fax: (+1) 626-564-9297
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  • Brian M. Stoltz Prof.

    1. Division of Chemistry and Chemical Engineering and the Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125 (USA)
    2. Department of Molecular Medicine, Beckman Research Institute at City of Hope, Duarte, CA 91001 (USA), Fax: (+1) 626-564-9297
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  • We wish to thank the California TRDRP (postdoctoral fellowships to X.H. and S.K.), Abbott Laboratories, Amgen, Merck, Bristol-Myers Squibb, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for X-ray crystallographic structure determination. Prof. David Horne is thanked for helpful discussions. The Bruker KAPPA APEX II X-ray diffractometer was purchased through an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance.

Abstract

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Aus 2 mach 1! Racemische tertiäre Halogenoxindole gehen im Zuge einer stereoablativen enantioselektiven Katalyse in enantiomerenangereicherte Oxindole mit quartären Kohlenstoffstereozentren über (siehe Schema). Durch Anwendung dieses Prozesses gelingt der schnelle asymmetrische Aufbau biologisch wichtiger Alkaloid-Gerüste.

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