HYPERVALENT IODINE-CATALYZED CYCLOADDITION OF NITRILE OXIDES TO ALKENES

被引：24
|
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
收藏
页码：682 / 688
页数：7
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