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Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence: Efficient Synthesis of Spirooxindole Pyrrolones.

A Rh(III)-catalyzed domino annulation of simple olefins with diazooxindole to give spirooxindole pyrrolone products was described. This reaction can be formally viewed as the result of an anomalous tandem C-H activation, carbene insertion, Lossen rearrangement and nucleophilic addition process. The potential utility of this reaction was further demonstrated by late-stage diversification of drug molecules.