1, 2-Silyl-Migrative Cyclization of Vinylsilanes Bearing a Hydroxy Group: Stereoselective Synthesis of Multisubstituted Tetrahydropyrans and Tetrahydrofurans1

…, S Okajima, T Nakagawa, T Takahashi…

Index: Miura, Katsukiyo; Hondo, Takeshi; Okajima, Shigeo; Nakagawa, Takahiro; Takahashi, Tatsuyuki; Hosomi, Akira Journal of Organic Chemistry, 2002 , vol. 67, # 17 p. 6082 - 6090

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Citation Number: 25

Abstract

Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R= alkyl) with 5 mol% TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis=> 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the CC double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis- ...

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