Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

Chun-Ting He; Xiao-Li Han; Yan-Xue Zhang; Zhen-Ting Du; Chang-Mei Si; Bang-Guo Wei

doi:10.1039/D0OB02158J

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Sc(OTf)₃-catalyzed [3 + 2]-cycloaddition of nitrones with ynones†

Chun-Ting He,^ab Xiao-Li Han,^a Yan-Xue Zhang,^a Zhen-Ting Du,

^b Chang-Mei Si

*^a and Bang-Guo Wei^a

Author affiliations

* Corresponding authors

^a Department of Natural Medicine, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, China
E-mail: sicm@fudan.edu.cn

^b College of Science, Northwest A&F University, 22 Xinong Road, Shaanxi, Yangling, China

Abstract

An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)₃-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa–11aw, 11ba–11la and 12aa–12ae in moderate to good yields.

This article is part of the themed collections: Synthetic methodology in OBC and Catalysis & biocatalysis in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB02158J
Article type: Paper
Submitted: 28 Oct 2020
Accepted: 03 Dec 2020
First published: 09 Dec 2020

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Org. Biomol. Chem., 2021,19, 457-466

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Sc(OTf)₃-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

C. He, X. Han, Y. Zhang, Z. Du, C. Si and B. Wei, Org. Biomol. Chem., 2021, 19, 457 DOI: 10.1039/D0OB02158J

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Organic & Biomolecular Chemistry