Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3015-3032.DOI: 10.6023/cjoc202208032 Previous Articles     Next Articles

Special Issue: 不对称催化专辑

ACCOUNT

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a,b, 陈志敏a,b,*()   

  1. 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
  • 收稿日期:2022-08-24 修回日期:2022-09-18 发布日期:2022-11-02
  • 通讯作者: 陈志敏
  • 作者简介:

    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.

  • 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

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

Deng Zhua,b, Zhi-Min Chena,b()   

  1. 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
  • Received:2022-08-24 Revised:2022-09-18 Published:2022-11-02
  • Contact: Zhi-Min Chen
  • 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

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