Chiral Phosphoric Acid Catalyzed Asymmetric Desymmetrization of <i>para</i>-Quinamines with Isocyanates: Access to Functionalized Imidazolidin-2-one Derivatives.

Hu, Kai-Wen; You, Xiao; Wang, Jin-Zheng; Wen, Xiaoan; Sun, Hongbin; Xu, Qing-Long; Lai, Zengwei

Chiral Phosphoric Acid Catalyzed Asymmetric Desymmetrization of para-Quinamines with Isocyanates: Access to Functionalized Imidazolidin-2-one Derivatives.

Hu, Kai-Wen; You, Xiao; Wang, Jin-Zheng; Wen, Xiaoan; Sun, Hongbin; Xu, Qing-Long; Lai, Zengwei.

Afiliación

Hu KW; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
You X; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
Wang JZ; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
Wen X; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
Sun H; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
Xu QL; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, China.
Lai Z; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

Org Lett ; 23(20): 7873-7877, 2021 10 15.

Article en En | MEDLINE | ID: mdl-34581589

RESUMEN

The development of enantioselective desymmetrization of para-quinamines with isocyanates catalyzed by chiral phosphoric acid is reported. The strategy provides concise access to functionalized imidazolidin-2-one derivatives in high yields and enantioselectivities under mild reaction conditions. Remarkably, this reaction could be performed on a gram scale using 5 mol % catalyst loading and the chiral imidazolidin-2-one derivatives could be easily transformed into valuable scaffolds without disturbing the enantiopurity, demonstrating the synthetic utility of this protocol.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2021 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos

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