Cycloadditions of Allylsilanes, Part 7.10 Stereoselective Synthesis of Hydroxycyclopentanes from Silylcyclopentanes by Oxidative Cleavage of the Carbon-Silicon Bond

All articles of this category 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