Acid-Catalyzed Cyclization of Vinylsilanes Bearing an Amino Group. Stereoselective Synthesis of Pyrrolidines1

…, T Hondo, T Nakagawa, T Takahashi, A Hosomi

Index: Miura, Katsukiyo; Hondo, Takeshi; Nakagawa, Takahiro; Takahashi, Tatsuyuki; Hosomi, Akira Organic Letters, 2000 , vol. 2, # 3 p. 385 - 388

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Citation Number: 52

Abstract

In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl) pyrrolidines 2. This cyclization was utilized for the stereoselective synthesis of 2, n-disubstituted pyrrolidines (n= 3-5). The cyclized products could be converted to the corresponding alcohols by oxidative cleavage of the carbon-silicon bond with TBAF and H2O2.

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