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碘化镁催化的供体-受体环丙烷与吲哚啉-2-硫酮的亲核开环反应

MgI-Catalyzed Nucleophilic Ring-Opening Reactions of Donor-Acceptor Cyclopropanes with Indoline-2-thiones.

作者信息

Tang Pan, Wei You-Yuan, Wen Long, Ma Hao-Jie, Yang Yi, Jiang Yan

机构信息

School of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong 643000, China.

出版信息

J Org Chem. 2022 Aug 19;87(16):10890-10901. doi: 10.1021/acs.joc.2c01179. Epub 2022 Aug 2.

Abstract

MgI-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as easy-to-handle sulfur nucleophiles were investigated. A series of functionalized γ-indolylthio butyric acid derivatives were synthesized in good to excellent yields under mild reaction conditions. Furthermore, the thioether functionalized ring-opening products could be transformed to sulfone and methionine analogues.

摘要

研究了以吲哚啉-2-硫酮作为易于处理的硫亲核试剂,在碘化镁催化下供体-受体环丙烷的亲核开环反应。在温和的反应条件下,以良好至优异的产率合成了一系列功能化的γ-吲哚基硫代丁酸衍生物。此外,硫醚功能化的开环产物可以转化为砜和蛋氨酸类似物。

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