Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3431-3447.DOI: 10.6023/cjoc202103046 Previous Articles     Next Articles



朱海梦a, 王超b,*(), 宗利利a,*()   

  1. a 厦门大学药学院 厦门 361102
    b 南京工业大学先进化学制造研究院 南京 211816
  • 收稿日期:2021-03-25 修回日期:2021-04-28 发布日期:2021-06-17
  • 通讯作者: 王超, 宗利利
  • 基金资助:
    国家自然科学基金(21802018); 福建省对外合作(2020I0003)

Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides

Haimeng Zhua, Chao Wangb(), Lili Zonga()   

  1. a School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102
    b Institute of Advanced Synthesis, Nanjing Tech University, Nanjing 211816
  • Received:2021-03-25 Revised:2021-04-28 Published:2021-06-17
  • Contact: Chao Wang, Lili Zong
  • Supported by:
    National Natural Science Foundation of China(21802018); Fujian Provincial Joint Research Project(2020I0003)

Sulfoxide compounds bearing unique sulfinyl group have attracted extensive attentions due to their important application in asymmetric organic synthesis and medicinal chemistry. The utility of chiral sulfoxides as versatile auxiliaries, ligands, and catalysts and synthons has been well demonstrated. Furthermore, the sulfinyl moiety can act as a pharmaceutical core, a bioisosteric replacement of the carbonyl moiety or a modifier in drug design and drug development. In this review, their biological activities with esomeprazole, ajoene, sulforaphane, sulforaphene, cenicriviroc, arbidol sulfoxide, armodafinil and so on are exemplified. And their mechanisms of action are illustrated briefly. Since the sulfur chirality is different from carbon stereogenic center, much effort has been devoted to the preparation of chiral sulfoxides. Herein the advances in asymmetric synthesis of sulfoxide during the past decade are presented. The direct asymmetric oxidation of prochiral sulfides with cheap iron-complex catalyst, polyoxometalates, organocatalyst, biocatalyst and electrocatalyst is discussed. Moreover, the complementary strategy based on sulfenate anions and miscellaneous strategies emerged recently are described. Additionally, our recent research works in the construction of chiral sulfoxide are also mentioned.

Key words: bioactive sulfoxide, sulfoxide drug, asymmetric synthesis, sulfoxidation, sulfenate anion, polyoxometalates