Magnesium bromide promoted barbier-type intramolecular cyclization of halo-substituted acetals, ketals, and orthoesters

被引：15

作者：

Huang, JW ^{[1
]}

Chen, CD ^{[1
]}

Leung, MK ^{[1
]}

机构：

[1] Natl Taiwan Univ, Dept Chem, Taipei 10764, Taiwan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(99)01813-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although acetals, ketals and orthoesters are commonly used as protective groups against organometallic reagents, Grignard reagents derived from halo-acetals, ketals, or orthoesters cyclize intramolecularly under MgBr2 promoted conditions, giving rise to the corresponding cycloalkanol and cycloalkanone derivatives. Our results also suggest a Lewis acid catalyzed push-pull mechanism operating for the cyclization. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：8647 / 8650

页数：4

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