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Nicholas R. Babij and Prof. John P. Wolfe Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas Angewandte Chemie International Edition 52

Article first published online: 3 JUL 2013 | DOI: 10.1002/anie.201302720

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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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