Enantioselective Azidothiolation and Oxythiolation of N-Allyl Sulfonamides and Organoselenium-Catalyzed Aza-Wacker Reactions
Congratulations! The publication of our group in ACS Catalysis , "Enantioselective Construction of Chiral Sulfides via Catalytic Electrophilic Azidothiolation and Oxythiolation of N-Allyl Sulfonamides" has been published recently (Yaoyu Liang, and Xiaodan Zhao* ACS Catal., 2019, 9, 6896-6902).
An efficient and convenient pathway was developed for enantioselective synthesis of chiral sulfides by chiral bifunctional selenide-catalyzed electrophilic azidothiolation and oxythiolation of N-allyl sulfonamides. By this protocol, a variety of chiral vicinal azidosulfides and oxysulfides were obtained in good yields with high enantioselectivities and diastereoselectivities. In this transformation, not only electrophilic arylthiolating reagents but also a wide range of electrophilic alkylthiolating reagents worked very well. The practical application of this method was elucidated by further transformations of the products into the diversified compounds.
Congratulations! The publication of our group in Synlett, "Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide" has been published recently (Huimin Li, Lihao Liao, and Xiaodan Zhao* Synlett, 2019, 30, 1688-1692).This paper was an invited contribution as part of the Cluster: Organosulfur and Organoselenium Compounds in Catalysis.
An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.
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