Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones

Xuanyu Shen, Andrey Shatskiy, Yan Chen, Markus D. Kärkäs*, Xiang-Shan Wang and Jian-Quan Liu*

*KTH Royal Institute of Technology, Stockholm SE-100 44, Sweden; Jiangsu Normal University, Xuzhou, Jiangsu 221116, China, Email: karkaskth.se, liujq316jsnu.edu.cn

X. Shen, A. Shatskiy, Y. Chen, M. D. Kärkäs, X.-S. Wang, J.-Q. Liu, J. Org. Chem., 2020, 85, 3560-3567.

DOI: 10.1021/acs.joc.9b03279

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Abstract

A silver oxide catalyzed [3 + 2] annulation of nitrones with isocyanides provides a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in very good yields in the presence of oxygen as the terminal oxidant.

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proposed mechanism

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Key Words

N-heterocycles, O-heterocycles, oxygen

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ID: J42-Y2020