Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides

Zanjiao Liu, Siqiang Fang, Haoze Li, Chunxiu Xiao, Kai Xiao, Zhishan Su () and Tianli Wang ()
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Zanjiao Liu: Sichuan University
Siqiang Fang: Sichuan University
Haoze Li: Sichuan University
Chunxiu Xiao: Sichuan University
Kai Xiao: Sichuan University
Zhishan Su: Sichuan University
Tianli Wang: Sichuan University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract The enantioselective synthesis of S-stereogenic sulfinamides has garnered considerable attention due to their structural and physicochemical properties. However, catalytic asymmetric synthesis of sulfinamides still remains daunting challenges, impeding their broad application in drug discovery and development. Here, we present an approach for the synthesis of S-stereogenic sulfinamides through peptide-mimic phosphonium salt-catalyzed asymmetric skeletal reorganization of simple prochiral and/or racemic sulfoximines. This methodology allows for the facile access to a diverse array of substituted sulfinamides with excellent enantioselectivities, accommodating various substituent patterns through desymmetrization or parallel kinetic resolution process. Mechanistic experiments, coupled with density functional theory calculations, clarify a stepwise pathway involving ring-opening and ring-closing processes, with the ring-opening step identified as crucial for achieving stereoselective control. Given the prevalence of S-stereogenic centers in pharmaceuticals, we anticipate that this protocol will enhance the efficient and precise synthesis of relevant chiral molecules and their analogs, thereby contributing to advancements in drug discovery.

Date: 2024
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DOI: 10.1038/s41467-024-48727-x

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