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Nadine V. Hanhan, Nicolas R. Ball-Jones, Ngon T. Tran and Prof. Annaliese K. Franz Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles Angewandte Chemie International Edition 51

Version of Record online: 12 DEC 2011 | DOI: 10.1002/anie.201105739

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Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl2(SbF6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si[BOND]C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

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