Chinese Journal of Organic Chemistry >
Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes
Received date: 2020-10-05
Revised date: 2020-11-03
Online published: 2020-12-05
Supported by
the National Natural Science Foundation of China(21901261); the National Natural Science Foundation of China(21772239); the China Postdoctoral Science Foundation(2018M633207); the Fundamental Research Funds for the Central Universities(20lgzd21); the Fundamental Research Funds for the Central Universities(20lgpy81)
Chiral organosulfur compounds have a wide range of applications in the fields of medicinal chemistry and asymmetric synthesis. The development of new methods for the preparation of these compounds is an important task in organic synthetic chemistry. Enantioselective electrophilic thiolation of alkenes has emerged as a straightforward pathway for the synthesis of chiral sulfides. By this fashion, both the thio group and another valuable functional group can be introduced simultaneously into the parent alkene molecules. We designed and synthesized a series of chiral bifunctional chalcogenide catalysts and successfully applied them to intra- and inter-molecular enantioselective trifluoromethylthiolation, alkylthiolation, arylthiolation of different kinds of alkenes. A variety of chiral sulfides were obtained with high enantioselectivities. The recent advances in chiral bifunctional chalcogenide catalyzed enantioselective thiofunctionalization of alkenes developed by our group are summarized, and the prospect of this field is also discussed.
Quanbin Jiang , Xiaodan Zhao . Chiral Bifunctional Chalcogenide-Catalyzed Enantioselective Electrophilic Thiofunctionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 443 -454 . DOI: 10.6023/cjoc202010005
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