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Synlett 1998; 1998(6): 613-616
DOI: 10.1055/s-1998-1727
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Cycloadditions of Allylsilanes, Part 11. Stereoselective Synthesis of Hydroxycyclopentanes and Hydroxymethylcyclobutanes by Titanium Tetrachloride-Promoted [3+2] and [2+2] Cycloadditions of Sterically Hindered Allylsilanes and Subsequent Oxidative Cleavage of the Carbon-Silicon Bond

Hans-Joachim Knölker* , Peter G. Jones, Günter Wanzl
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany; Fax + 49(7 21)69 85 29; E-mail: knoe@ochhades.chemie.uni-karlsruhe.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Even highly sterically hindered organosilicon compounds containing the bulky tert-butyldiphenylsilyl group can be oxidatively cleaved to the corresponding carbinols using a modified protocol of the original Fleming-Tamao oxidation that generates the intermediate tert-butyldifluorosilyl derivatives. This novel application emphasizes the utility of allyl-tert-butyldiphenylsilane as a building block for the stereoselective synthesis of either hydroxycyclopentanes or hydroxymethylcyclobutanes via the sequence titanium tetrachloride-promoted cycloaddition and oxidative cleavage.

allylsilanes - titanium tetrachloride - cycloadditions - oxidative cleavage - tert-butyldiphenylsilyl derivatives