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2022 , Vol. 42 >Issue 10: 3015 - 3032

DOI: https://doi.org/10.6023/cjoc202208032

研究专题

手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用

  • 朱登 ,
  • 陈志敏
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  • a 上海交通大学化学化工学院 上海 200240
    b 上海市手性药物分子工程重点实验室 上海 200240

朱登, 2019年在浙江工业大学获得学士学位, 现为上海交通大学博士研究生, 导师为陈志敏副教授, 主要研究方向为手性含硫化合物的高效合成.

陈志敏, 博士, 长聘教轨副教授, 上海市高校特聘教授(东方学者). 2009年在福州大学获学士学位, 2014年在兰州大学获有机化学博士学位, 导师涂永强教授. 2014~2017年在上海交通大学(导师: 涂永强教授)从事博士后研究, 期间2015~2017在美国犹他大学(导师: Matthew S. Sigman教授)从事博士后研究. 2017年底加入上海交通大学化学化工学院, 开展独立研究, 主要围绕手性硫化学和硒化学开展研究工作, 通过发展新催化剂、新试剂、新策略实现各种手性硫化合物、硒化合物的高效合成.

收稿日期: 2022-08-24

  修回日期: 2022-09-18

  网络出版日期: 2022-09-23

基金资助

国家自然科学基金(21871178); 国家自然科学基金(22071149); 上海市科学技术委员会(19JC1430100); 上海高校特聘教授(东方学者)资助项目

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Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides

  • Deng Zhu ,
  • Zhi-Min Chen
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  • a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
    b Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240
* Corresponding authors.

Received date: 2022-08-24

  Revised date: 2022-09-18

  Online published: 2022-09-23

Supported by

National Natural Science Foundation of China(21871178); National Natural Science Foundation of China(22071149); Science & Technology Department of Shanghai(19JC1430100); Program for Professor of Special Appointment(Eastern Scholar) at Shanghai Institutions of Higher Learning

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摘要

手性含硫化合物不仅是有机合成领域重要的中间体和催化剂, 许多天然产物和临床药物也都是手性含硫化合物. 因此, 发展手性含硫化合物的高效合成方法一直是有机合成化学的重要研究课题, 其中不对称亲电硫化反应近年来受到化学家的广泛关注. 氢键相互作用可以在化合物的生成过程中提供很高的灵活性, 已经逐渐成为不对称催化中的有力工具. 受此启发, 本课题组开发了一类基于氢键相互作用的路易斯碱/布朗斯特酸协同催化策略, 并成功将其应用于多种类型烯烃的分子内和分子间的不对称芳硫基化反应, 以及芳基化合物的不对称芳硫基取代反应, 高效地合成了各种手性含硫化合物. 总结了我们课题组利用基于氢键相互作用的路易斯碱/布朗斯特酸协同催化策略在不对称亲电芳硫基化反应中的研究进展, 并对其未来发展进行了展望.

关键词： 氢键相互作用; 协同催化; 路易斯碱; 布朗斯特酸; 分子间反应; 烯烃双官能团化; 手性硫化合物; 阻转异构

本文引用格式

朱登 , 陈志敏 . 手性路易斯碱/布朗斯特酸协同催化策略在有机硫化物不对称合成中的应用[J]. 有机化学, 2022 , 42(10) : 3015 -3032 . DOI: 10.6023/cjoc202208032

Abstract

Chiral organosulfur compounds are not only important synthetic intermediates and catalysts in the field of organic synthesis, but also widely exist in many natural products and clinical drugs. The development of efficient synthesis of chiral organosulfur compounds has always been an important research topic in organic synthetic chemistry, in which enantioselective electrophilic sulfenylation reactions have attracted significant attention in recent years. Hydrogen bond interactions provide much flexibility in the preorganization of compounds and have gradually become a powerful tool in asymmetric catalysis. Inspired from this, our group developed a type of Lewis base/Brønsted acid synergistic catalysis strategy based on the hydrogen bonding interaction, and successfully applied it to intra- and inter-molecular asymmetric sulfenylation of different kinds of alkenes, and enantioselective sulfenylation substitution reactions of aryl compounds. A variety of chiral organosulfur compounds were obtained with high efficiency. The recent advances of enantioselective electrophilic arylthiolation reactions using novel synergistic catalysis strategy developed by our group are summarized, and the prospect of this research topic is also discussed.

Key words： hydrogen bonding interaction; synergistic catalysis; Lewis base; Brønsted acid; intermolecular reaction; alkene difunctionalization; chiral sulfide; atropisomerism

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