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 CN and a CC 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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Babij et al. (2013) studied this question.
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