Chinese Journal of Organic Chemistry >
Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides
Received date: 2021-03-25
Revised date: 2021-04-28
Online published: 2021-06-17
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.
Haimeng Zhu , Chao Wang , Lili Zong . Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3431 -3447 . DOI: 10.6023/cjoc202103046
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