Acid-catalyzed rearrangement of α-hydroxycyclopropylsilanes

被引：17

作者：

Sakaguchi, K ^{[1
]}

Fujita, M ^{[1
]}

Ohfune, Y ^{[1
]}

机构：

[1] Osaka City Univ, Dept Mat Sci, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

acid-catalyzed rearrangement; alpha-hydroxycyclopropylsilane; cyclobutyl cation; 1,2]-CC bond migration;

D O I：

10.1016/S0040-4039(98)00760-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acidic treatment of the (1S,1'S,2'R)-alpha-hydroxycyclopropylsilane 1 gave a mixture of rearranged products, which were composed of the ring-opened (S)-vinylsilane 3, the tandem [1,2]-CC bond migration product (1S,2R,1'S)-silylcyclopropane 4, and its 1'R isomer 5, respectively. Hence, the use of the 2'S isomer 2 produced a mixture of the (R)-3, 4, and 5, Our proposed mechanisms of the present cationic rearrangement are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：4313 / 4316

页数：4

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