Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles

Authors


  • This research was supported by the University of California, Davis and the Donors of the American Chemical Society Petroleum Research Fund (49I8I-DNI1). A.K.F. acknowledges the 3M Corporation for a Nontenured Faculty Award. N.V.H. is a recipient of the Eugene Cota-Robles, the Bradford Borge, and the Bryan Miller Graduate Fellowships, and N.T.T. is a recipient of the Bradford Borge Chemistry Fellowship and a Department of Education GAANN Fellowship. We would also like to acknowledge Dr. James C. Fettinger for consultations regarding X-ray analysis.

Abstract

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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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