HYPERVALENT IODINE-CATALYZED CYCLOADDITION OF NITRILE OXIDES TO ALKENES

被引：25

作者：

Xiang, Changbin ^{[1
]}

Li, Tingting ^{[1
]}

Yan, Jie ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310032, Zhejiang, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 05期

关键词：

Catalytic reaction; cycloaddition; hypervalent iodine intermediate; iodobenzene; isoxazoline; HYDROXIMOYL CHLORIDES; POTENT INHIBITORS; BENZISOXAZOLES; ISOXAZOLINES; DERIVATIVES; OXIDATIONS; GENERATION; ALDOXIMES; CHEMISTRY; OXIMES;

D O I：

10.1080/00397911.2013.834364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was first oxidized into the hypervalent iodine intermediate by m-chloroperbenzoic acid, which then transformed aldoximes into nitrile oxides, and a 1,3-dipolar cycloaddition of nitrile oxides to alkenes to provide the isoxazolines in moderate to good yields. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

引用

页码：682 / 688

页数：7

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