STEREOSELECTIVE SYNTHESIS OF VINYL ETHERS BY THE REACTION OF N-(ARYLIDENE(OR ALKYLIDENE)AMINO)-2-AZETIDINONES WITH OZONE

被引：13

作者：

ALCAIDE, B

PEREZCASTELLS, J

POLANCO, C

SIERRA, MA

机构：

[1] Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 19期

关键词：

D O I：

10.1021/jo00124a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.

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页码：6012 / 6016

页数：5

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