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Synlett 1995; 1995(4): 378-382
DOI: 10.1055/s-1995-4950
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Cycloadditions of Allylsilanes, Part 7.10 Stereoselective Synthesis of Hydroxycyclopentanes from Silylcyclopentanes by Oxidative Cleavage of the Carbon-Silicon Bond

Hans-Joachim Knölker* , Günter Wanzl
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany
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Publication Date:
31 December 2000 (online)

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Oxidative cleavage of methyldiphenylsilyl- and triphenylsilylcyclopentanes has been achieved by protodesilylation using boron trifluoride/acetic acid and TBAF followed by oxidation with hydrogen peroxide. Nucleophilic substitution of the initially formed fluorosilane by methanol and water during the Tamao oxidation is demonstrated.

allylsilanes - [3+2] cycloaddition - protodesilylation - Tamao oxidation - hydroxycyclopentane

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