TUNGSTATE-CATALYZED OXIDATION OF SECONDARY-AMINES TO NITRONES - ALPHA-SUBSTITUTION OF SECONDARY-AMINES VIA NITRONES

被引：302

作者：

MURAHASHI, SI

MITSUI, H

SHIOTA, T

TSUDA, T

WATANABE, S

机构：

[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 06期

关键词：

D O I：

10.1021/jo00293a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sodium tungstate catalyzed oxidation of secondary amines with hydrogen peroxide gives the corresponding nitrones. Acyclic and cyclic nitrones can be obtained from secondary amines in a single step in good to excellent yields. The oxidation of secondary amines in the presence of alkenes gives isoxazolidines by 1,3-dipolar cycloaddition of nitrones. Introduction of a substituent at the 03B1-position of secondary amines can be performed upon oxidation of secondary amines and subsequent treatment with various nucleophiles. © 1990, American Chemical Society. All rights reserved.

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页码：1736 / 1744

页数：9

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