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Bifunctional Squaramide-Catalyzed Oxidative Kinetic Resolution: Simultaneous Access to Axially Chiral Thioether and Sulfoxide.
Wen, Wei; Yang, Chang-Lin; Wu, Zhu-Lian; Xiao, Dong-Rong; Guo, Qi-Xiang.
Afiliación
  • Wen W; Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing Key Laboratory of Soft-Matter Material Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
  • Yang CL; School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
  • Wu ZL; School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
  • Xiao DR; School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
  • Guo QX; Key Laboratory of Applied Chemistry of Chongqing Municipality, Chongqing Key Laboratory of Soft-Matter Material Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
Adv Sci (Weinh) ; 11(28): e2402429, 2024 Jul.
Article en En | MEDLINE | ID: mdl-38751149
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Adv Sci (Weinh) Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Adv Sci (Weinh) Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania