(3 + 1) Annulation/Rearrangement Cascade of C,N-Cyclic Azomethine Imines and 3-Chlorooxindoles: Construction of Hexahydroindeno[2,1-c]pyrazole Spirooxindole Frameworks.

The Brønsted base promoted (3 + 1) annulation reaction of C,N-cyclic azomethine imines and 3-chlorooxindoles was investigated, finally delivering complex hexahydroindeno[2,1-c] pyrazoles incorporating a spirocyclic oxindole motif after an unexpected rearrangement process. The asymmetric version of this new transformation could be accomplished, but slow racemization of the chiral product was observed at ambient temperature. Experiments and DFT calculations were further conducted to elucidate the reaction process and racemization mechanism.