A new strategy for synthesis of attached rings

被引：37

作者：

Overman, LE ^{[1
]}

Pennington, LD ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2000年 / 78卷 / 06期

关键词：

Prins cyclization; pinacol rearrangement; attached rings;

D O I：

10.1139/cjc-78-6-732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first investigation of the use of pinacol-terminated Prins cyclizations to form attached rings is reported. Treatment of triisopropylsilyl ethers of (Z)- or (E)-[2-(6,6-dimethoxyhexylidene)cyclohexanol with SnCl4 provides bicyclic products having attached rings. The approach is synthetically useful in the Z alkylidenecyclohexane series, proceeding selectively by a pathway involving carbon migration in the pinacol rearrangement step, to provide methoxy epimers of 1-(2-methoxycyclohexyl)cyclopentylcarboxaldehyde. Reaction of the corresponding E stereoisomer is more complex and yields a mixture of products resulting from both hydride and carbon migration in the pinacol rearrangement step.

引用

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页码：732 / 738

页数：7

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