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

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/Bronsted 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.

Automated summary

Chiral organosulfur compounds are important in organic synthesis and medicine. The enantioselective electrophilic sulfenylation reactions have gained significant attention recently. Through hydrogen bonding interactions, the Lewis base/Bronsted acid synergistic catalysis strategy has been developed for the efficient synthesis of chiral organosulfur compounds, as well as for asymmetric sulfenylation and substitution reactions.