Synthesis of Isoxazoline/Cyclic Nitrone-Featured Methylenes Using Unsaturated Ketoximes: A Dual Role of TEMPO

被引：65

作者：

Chen, Fei ^{[1
]}

Yang, Xiu-Long ^{[1
]}

Wu, Zhi-Wei ^{[1
]}

Han, Bing ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期

关键词：

BOND-DISSOCIATION ENTHALPIES; RADICAL CYCLIZATION; ALPHA-METHYLENATION; UNACTIVATED ALKENES; OXIMES; CONSTRUCTION; PYRAZOLINES; TRANSITION; GENERATION; OXIDATION;

D O I：

10.1021/acs.joc.6b00180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, metal-free, and regioselective approach for the synthesis of isoxazoline/cyclic nitrone-featured methylenes has been developed by the reaction of readily accessible beta,gamma- and gamma,delta-unsaturated ketoximes with TEMPO via tandem iminoxyl radical-promoted cyclization/TEMPO-mediated Cope-like elimination, respectively. This protocol utilizes commercially available TEMPO as the iminoxyl radical initiator as well as the beta-hydrogen acceptor in the Cope-like elimination.

引用

页码：3042 / 3050

页数：9

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