Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropyl ketones

被引：22

作者：

Peron, GLN

Kitteringham, J

Kilburn, JD ^{[1
]}

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] SmithKline Beecham Pharmaceut, Dept Synthet Chem, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 10期

关键词：

methylenecyclopropane; Lewis acid; cascade; cyclisation;

D O I：

10.1016/S0040-4039(99)02342-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid mediated cyclisation of various silyl-substituted methylenecyclopropyl ketones has been investigated. The presence of the silyl-substituent enhances the reactivity of the methylene cyclopropane in comparison to our earlier study on non-silyl-substituted methylenecyclopropyl ketones, allowing milder Lewis acids (BF3 . Et2O or BF3 . 2AcOH) to be used for the cyclisation reaction. The mild conditions used allow the allyl cation, formed as an intermediate in the cyclisation, to be trapped in further carbon-carbon bond-forming reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1615 / 1618

页数：4

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