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

doi:10.1055/s-1998-1727

Synlett 1998; 1998(6): 613-616
DOI: 10.1055/s-1998-1727

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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

PDF (66 kb)