The cyclopropylmethylsilane terminated prins reaction:: Stereoelectronic controlled formation of (E)-skipped dienes alcohols and a (Z)-skipped diene modification

被引：12

作者：

Braddock, DC ^{[1
]}

Badine, DM ^{[1
]}

Gottschalk, T ^{[1
]}

Matsuno, A ^{[1
]}

Rodriguez-Lens, M ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

SYNLETT | 2003年 / 03期

关键词：

prins; skipped dienes; stereoelectronic; buttressing; cyclopropylmethyl cation;

D O I：

10.1055/s-2003-37111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1-phenyldimethylsilyl-2-vinyl cyclopropane with aldehydes under the influence of dimethylaluminium chloride proceeds smoothly to provide skipped diene alcohols with exclusive E-olefin geometry regardless of the initial cis/trans configuration of the starting cyclopropane. The reaction is under stereoelectronic control where the Prins cation favours an anti-bisected conformation. A syn-bisected conformation can be partially induced by the introduction of a buttressing trimethylsilyl group on the cyclopropane ring, leading to competitive (masked) Z-skipped diene formation.

引用

页码：345 / 348

页数：4

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