4.4 Article

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group. Benzyldimethylsilyl group as an effective promoter and novel hydroxy surrogate

Journal

TETRAHEDRON LETTERS
Volume 41, Issue 13, Pages 2129-2132

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)00091-5

Keywords

cyclization; acid catalyst; silicon and compound; oxidation

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A benzyldimethylsilyl (BnDMS) group was found to effectively enhance the reactivity of vinylsilanes toward the acid-catalyzed intramolecular addition of a hydroxy group in comparison with a dimethylphenylsilyl group. The BnDMS group of the resultant cyclized products could be easily converted to a hydroxy group by the action of TBAF-H2O2-KHCO3. (C) 2000 Elsevier Science Ltd. All rights reserved.

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