Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides

Abstract

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.

Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers

“…Synthesis of enantioenriched sulfoxides with chiral transition-metal catalysts is well studied and summarized in previous reviews. ,− Notable enantioselective oxidation systems are those using Ti­(O- i Pr) 4 as the catalyst and modulate with different chiral ligands such as diethyl tartrate, BINOL, salen, Schiff base, and porphyrin. These ligands are also well studied with many other metals such as Al, V, Cu, and Fe.…”

Synthesis of Heterobenzyl Sulfoxides Enabled by Palladium-Catalyzed Allylic Alkylation of Sulfenate Anions with Allenamides

“…Sulfoxides are an important class of compounds, which not only are widely utilized as versatile building blocks in organic synthesis but also presented in drugs and natural products . Given the importance and unique properties of sulfoxides (Figure ), the construction of benzylic sulfoxides has become an important research topic in organic chemistry . During the past decades, the direct oxidation of sulfides and the nucleophilic substitution of sulfinyl derivatives with reactive organolithium or Grignard reagents have been developed for the synthesis of sulfoxide-containing molecular frames. , However, the disadvantages of these methods include harsh reaction conditions, the use of sensitive reagents, and limited functional group tolerance.…”