Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones

被引：176
作者：
Han, Bing [1 ]
Yang, Xiu-Long [1 ]
Fang, Ran [1 ]
Yu, Wei [1 ]
Wang, Chao [1 ]
Duan, Xiao-Yong [1 ]
Liu, Shuai [1 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 35期
关键词：
alkenes; cyclization; heterocycles; radicals; synthetic methods; ELECTRON-SPIN-RESONANCE; BOND-DISSOCIATION ENTHALPIES; AEROBIC OXIDATIVE SYNTHESIS; IMINOXY; EFFICIENT; AZODICARBOXYLATE; ISOMERIZATION; CYCLIZATION; EXTENSIONS; CHEMISTRY;
D O I：
10.1002/anie.201203799
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Up the tempo: The intramolecular addition of oxime radicals to C=C bonds was achieved by using DEAD and TEMPO to give 4,5-dihydroisoxazoles as a result of a C=O bond-forming, 5-exo-trig cyclization. γ,δ-Unsaturated ketoximes also reacted to afford cyclic nitrones through C-N bond formation. The reactions offer a metal-free approach for the vicinal difunctionalization of unactivated alkenes. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8816 / 8820
页数：5
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