SYNTHESIS OF HETEROCYCLIC-COMPOUNDS BY THE ORGANOTIN ALKOXIDE PROMOTED CLEAVAGE OF GAMMA-BROMO BETA-LACTONES

被引：32

作者：

SHIBATA, I

TOYOTA, M

BABA, A

MATSUDA, H

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Suita

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 08期

关键词：

D O I：

10.1021/jo00295a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 2-oxazolidinones are prepared in good to excellent yields by the organotin alkoxide promoted ring cleavage of γ-bromo β-lactones. This reaction proceeds via the key organotin haloalkoxide intermediate, which reacts with an isocyanate followed by cyclization. Stereoisomerically pure products are obtained by combination with the stereoselective bromolactonization reaction. Moreover, other heterocumulenes such as RN=C=NR, RN=C=S, C02, and γ-bromo β-lactam are used as substrates. © 1990, American Chemical Society. All rights reserved.

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页码：2487 / 2491

页数：5

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