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Keywords:

  • alkaloids;
  • asymmetric catalysis;
  • desymmetrization;
  • heterocycles;
  • palladium
Thumbnail image of graphical abstract

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.