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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.

DOI:10.1021/acs.joc.9b03279
PMID:32013428
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7307928/
Abstract

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.

摘要

已开发出一种银辅助的硝酮与异腈进行[3 + 2]环化反应的方法。所开发的方案使用氧化银作为催化剂、分子氧作为终端氧化剂，能够以良好至优异的产率获得各种2,3,4-三取代的1,2,4-恶二唑烷-5-酮衍生物单一非对映异构体。基于实验结果提出了一种涉及亲核加成/环化/脱银质子化/氧化途径的合理机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/18f479247d9a/jo9b03279_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/63b9385011dd/jo9b03279_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/9caeb4654c34/jo9b03279_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/55b14ef7cf20/jo9b03279_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/3de232ba5ad5/jo9b03279_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/18f479247d9a/jo9b03279_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/63b9385011dd/jo9b03279_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/9caeb4654c34/jo9b03279_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/55b14ef7cf20/jo9b03279_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/3de232ba5ad5/jo9b03279_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7021/7307928/18f479247d9a/jo9b03279_0005.jpg

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