Formation of seven-membered oxacycles through ring expansion of cyclopropanated carbohydrates

被引：61

作者：

Hoberg, JO

机构：

[1] National Renewable Energy Laboratory, Golden, CO 80401

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 19期

关键词：

D O I：

10.1021/jo970649v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclopropanation and ring expansion of 4,6-O-(di-tert-butylsilanediyl)-D-glucal (1) to produce oxepanes have been investigated. Using catalytic amounts of TMSOTf and an excess of a silylated nucleophile, a wide range of substituted oxepanes have been synthesized. Good to excellent yields are obtained; however, only modest diastereoselectivity resulted. This new methodology should provide convenient access into the synthesis of optically active oxepanes.

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页码：6615 / 6618

页数：4

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