A NEW APPROACH TO THE SYNTHESIS OF MONOCYCLIC BETA-LACTAM DERIVATIVES

被引：27

作者：

AHN, C ^{[1
]}

KENNINGTON, JW ^{[1
]}

DESHONG, P ^{[1
]}

机构：

[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLLEGE PK,MD 20742

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to the synthesis of monocyclic beta-lactam derivatives is presented. Dipolar cycloaddition of an aldonitrone with TMS-acetylene provided a 5-(trimethylsilyl)is oxazoline. The isoxazoline was fragmented with tetrabutylammonium fluoride (TBAF) to provide monocyclic beta-lactam derivatives in modest yield. Fragmentation of the isoxazoline with aqueous HF provides excellent yields of alpha,beta-unsaturated amides.

引用

页码：6282 / 6286

页数：5