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

Fei Chen, Xiu-Long Yang, Zhi-Wei Wu and Bing Han*

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China, Email: hanblzu.edu.cn

F. Chen, X.-L. Yang, Z.-W. Wu, B. Han, J. Org. Chem., 2016, 81, 3042-3050.

DOI: 10.1021/acs.joc.6b00180 (free Supporting Information)


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Abstract

The use of TEMPO enables a novel, metal-free, and regioselective approach for the synthesis of isoxazolines or cyclic nitrones substituted with methylene groups via tandem iminoxyl radical-promoted cyclization or TEMPO-mediated Cope-like elimination, respectively.

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TEMPO-Mediated Regioselective Synthesis of Isoxazoline/Cyclic Nitrone-Featured Methylenes



Key Words

2-isoxazolines, TEMPO


ID: J42-Y2016