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Issue 25, 2020
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Recent advances in the oxime-participating synthesis of isoxazolines

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Abstract

Isoxazoline compounds are used as important intermediates for the synthesis of organic molecules, which are widely used in the chemical and life science industries. Oxime-participating cyclization has emerged as an efficient strategy for the construction of isoxazolines. This review is devoted to highlighting the main achievements (since 2010) in the development of methodologies for the synthesis of isoxazolines. According to the reaction mechanism, the oxime-participating synthesis of isoxazolines can be mainly classified into four reaction types: iminoxyl radical-initiated intramolecular cyclization, intermolecular radical addition-initiated cyclization, intramolecular nucleophilic cyclization, and [3 + 2] cycloaddition. Meanwhile, miscellaneous examples are also illustrated, such as [2 + 2 + 1] cycloaddition. Representative reactions will be discussed for each of the highlighted synthetic strategies. In addition, the enantioselective synthesis of isoxazolines is also illustrated in this review.

Graphical abstract: Recent advances in the oxime-participating synthesis of isoxazolines

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Article information


Submitted
10 May 2020
Accepted
01 Jun 2020
First published
01 Jun 2020

Org. Biomol. Chem., 2020,18, 4709-4716
Article type
Review Article

Recent advances in the oxime-participating synthesis of isoxazolines

J. Liao, L. Ouyang, Q. Jin, J. Zhang and R. Luo, Org. Biomol. Chem., 2020, 18, 4709
DOI: 10.1039/D0OB00963F

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