Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hydroxy Group: A New Method for Stereoselective Synthesis of Disubstituted Tetrahydrofurans1

…, T Nakagawa, T Takahashi, A Hosomi

文献索引：Miura; Okajima; Hondo; Nakagawa; Takahashi; Hosomi Journal of the American Chemical Society, 2000 , vol. 122, # 46 p. 11348 - 11357

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被引用次数: 50

摘要

In the presence of a catalytic amount of TsOH or TiCl4,(Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the CC double bond strongly influence the cyclization rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, ...