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.
Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles†
Article first published online: 12 DEC 2011
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 4, pages 989–992, January 23, 2012
How to Cite
Hanhan, N. V., Ball-Jones, N. R., Tran, N. T. and Franz, A. K. (2012), Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles. Angew. Chem. Int. Ed., 51: 989–992. doi: 10.1002/anie.201105739
- Issue published online: 17 JAN 2012
- Article first published online: 12 DEC 2011
- Manuscript Received: 14 AUG 2011
- University of California, Davis. Grant Number: 49I8I-DNI1
- allylic compounds;
- asymmetric catalysis;
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 SiC bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.