银辅助的硝酮与异腈的[3 + 2]环化反应：2,3,4-三取代-1,2,4-恶二唑烷-5-酮的合成

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

作者信息

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

机构信息

School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Department of Chemistry, KTH Royal Institute of Technology, Stockholm SE-100 44, Sweden.

出版信息

J Org Chem. 2020 Mar 6;85(5):3560-3567. doi: 10.1021/acs.joc.9b03279. Epub 2020 Feb 20.

A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-5-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.