Internally Reuse Waste: Catalytic Asymmetric One-Pot Strecker Reaction of Fluoroalkyl Ketones, Anilines and TMSCN by Sequential Catalysis
Corresponding Author
Yun-Lin Liu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Current address: School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, Guangdong 510006, ChinaE-mail: [email protected]; [email protected]Search for more papers by this authorXiao-Ping Yin
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Search for more papers by this authorCorresponding Author
Jian Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yun-Lin Liu
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Current address: School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, Guangdong 510006, ChinaE-mail: [email protected]; [email protected]Search for more papers by this authorXiao-Ping Yin
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Search for more papers by this authorCorresponding Author
Jian Zhou
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 China
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200062 China
E-mail: [email protected]; [email protected]Search for more papers by this authorAbstract
We report a highly enantioselective one-pot facile synthesis of fluorinated Cα-tetrasubstituted amino nitriles from α-fluoroalkyl α-aryl ketones, anilines, and TMSCN through a sequential p-TsOH catalyzed ketimine formation and chiral bifunctional tertiary amine mediated asymmetric Strecker reaction. This one-pot approach has two important advantages. First, it greatly improves the overall yield of the synthesis of chiral Cα-tetrasubstituted fluorinated aminonitriles from ketones, because the purification of α-fluorinated ketimines by column chromatography suffers from great yield loss. Second, it represents the first example of asymmetric tandem reactions that can simultaneously reuse the by-product and catalyst from the upstream step as a promoter and an additive to improve the reactivity and enantioselectivity of the subsequent catalytic enantioselective reaction, respectively. It could utilize the by-product H2O generated in-situ from the ketimine formation step to activate TMSCN to form HCN, and concurrently reuse the remaining p-TsOH acid as an additive to improve enantioselectivity.
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