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Stereocontrolled Synthesis of Spirooxindoles through Lewis Acid-Promoted [5 + 2]-Annulation of Chiral Silyl Alcohols

The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.

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Bibliographic Details
Published in:Organic letters 2009-08, Vol.11 (15), p.3366-3369
Main Authors: Zhang, Yun, Panek, James S
Format: Article
Language:English
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Summary:The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901202t