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

被引：178

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

页码：8816 / 8820

页数：5

共 57 条

[1]

[Anonymous], 2011, ANGEW CHEM INT EDIT

[2] DI TERT BUTYLIMINOXY, A FREE RADICAL OF MODERATE STABILITY [J].