Chinese Journal of Organic Chemistry >
Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides
Received date: 2022-08-24
Revised date: 2022-09-18
Online published: 2022-09-23
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.
Deng Zhu , Zhi-Min Chen . Application of Chiral Lewis Base/Brønsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3015 -3032 . DOI: 10.6023/cjoc202208032
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