Generation, electrocyclic ring opening, and unprecedented conversion of a 3-acylaminoazetinone into cis-3,4-disubstituted azetidinones

被引：0

作者：

Wolfe, S ^{[1
]}

Ro, S ^{[1
]}

Shi, Z ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 08期

关键词：

rhodium carbene; torquochemical; azetinone; mercaptoazetidinone;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An attempt to synthesize the nucleus of cefaclor by insertion of an appropriately functionalized rhodium carbene into a beta -lactam N-H bond leads instead to attack at sulfur, followed by fragmentation into a four-membered thietanone and a four-membered 3-acylaminoazetinone. The azetinone undergoes electrocyclic ring opening, with a calculated half-life of 11 s at 40 degreesC, to a trans-disubstituted vinyl isocyanate, but can be trapped by saturated, unsaturated allylic and benzylic alcohols to form 3,4-disubstituted azetidinones in which the cis- isomer predominates.

引用

页码：1259 / 1271

页数：13