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One-Pot Synthesis of Isoxazolines from Aldehydes Catalyzed by Iodobenzene

Liuquan Han, Bijun Zhang, Changbin Xiang, Jie Yan*

*College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, P. R. of China, Email: jieyan87zjut.edu.cn

L. Han, B. Zhang, C. Xiang, J. Yan, Synthesis, 2014, 46, 503-509.

DOI: 10.1055/s-0033-1340464 (free Supporting Information)


Abstract

In a convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by an in situ generated hypervalent iodine compound. Finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes provides isoxazolines in good yields.

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Key Words

one-pot synthesis, isoxazolines, iodobenzene, hypervalent iodine compounds, MCPBA, catalytic cycloaddition, 1,3-dipolar cycloaddition


ID: J66-Y2014