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Enantioselective S-Alkylation of Sulfenamides With Copper-Catalyzed Amino-Radical-Transfer Deboronation
Ke Wang1, Yu Qi1, Menghui Ding1
1Department of Medicinal Chemistry, State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Shandong Key Laboratory of Druggability Optimization and Evaluation for Lead Compounds, School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong, China.
Abstract:
This work reports a copper-catalyzed enantioselective S-alkylation of sulfenamides enabled by an amino-radical-transfer deboronation pathway. Chiral sulfilimines are obtained in high yields (up to 95%) and enantioselectivities (up to 98% ee) under mild conditions. An isomerizable bis(oxazoline) ligand bearing a bridging CH2 unit is identified as the key factor for both reactivity and stereoselectivity in the copper-catalyzed radical-relay coupling with sulfenamides. The method offers a general platform for accessing enantioenriched S(IV) architectures with aliphatic substituents and demonstrates strong potential for applications in medicinal chemistry.
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