Bifunctional Squaramide‐Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide

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Abstract: Axially chiral thioethers and sulfoxides emerge as two pivotal classes of ligands and organocatalysts, which have remarkable features in the stereoinduction of various asymmetric transformations. However, the lack of easy methods to access such molecules with diverse structures has hampered their broader utilization. Herein, an oxidative kinetic resolution for sulfides using a chiral bifunctional squaramide as the catalyst with cumene hydroperoxide as the terminal oxidant is established. This asymmetric approach provides a variety of axially chiral thioethers as well as sulfoxides bearing both axial and central chirality, with excellent diastereo‐ and enantioselectivities. This catalytic system also successfully extends to the kinetic resolution of benzothiophene‐based sulfides. Preliminary mechanism investigation indicates that the multiple hydrogen bonding interactions between the bifunctional squaramide catalyst and substrates play a crucial role in determining the enantioselectivity and reactivity.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Bifunctional Squaramide‐Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide ; day:15 ; month:05 ; year:2024 ; extent:11
Advanced science ; (15.05.2024) (gesamt 11)

Creator: Wen, Wei
Yang, Chang‐Lin
Wu, Zhu‐Lian
Xiao, Dong‐Rong
Guo, Qi‐Xiang

DOI: 10.1002/advs.202402429

URN: urn:nbn:de:101:1-2405161420568.357626618395

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 22.08.20252025, 12:54 AM CEST

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Wen, Wei
Yang, Chang‐Lin
Wu, Zhu‐Lian
Xiao, Dong‐Rong
Guo, Qi‐Xiang

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Bifunctional Squaramide‐Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide

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