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Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas

Authors

  • Nicholas R. Babij,

    1. Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)
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  • Prof. John P. Wolfe

    Corresponding author
    1. Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)
    • Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)

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  • The authors acknowledge the NIH-NIGMS (GM 098314) and the University of Michigan Associate Prof. Support Fund for financial support of this work. Additional funding was provided by GlaxoSmithKline and Amgen.

Abstract

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Lost symmetry: Fused bicyclic ureas are enantioselectively obtained through Pd-catalyzed desymmetrizing carboaminations of meso-2,5-diallylpyrrolidinyl ureas (see scheme). The reactions generate a C[BOND]N and a C[BOND]C bond, and afford products with three stereocenters. One of these products was transformed to a tricyclic guanidine and then to 9-epi-batzelladine K over several steps.

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