Chiral Ag-Complex Catalyzed Enantioselective α-Functionalization of Cyclic Azomethine Ylides with Concomitant Remote-Controlled Asymmetric Desymmetrization of N-Arylmaleimides and Cyclopentene-1,3-diones
Ji-Hong Liu
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
Search for more papers by this authorJian-Mei Wang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
Search for more papers by this authorYan-Ping Zhang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorZhen-Hua Wang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorLei Yang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorJian-Qiang Zhao
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorCorresponding Author
Ming-Qiang Zhou
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorCorresponding Author
Yong You
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorCorresponding Author
Wei-Cheng Yuan
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorJi-Hong Liu
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
Search for more papers by this authorJian-Mei Wang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
Search for more papers by this authorYan-Ping Zhang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorZhen-Hua Wang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorLei Yang
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorJian-Qiang Zhao
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
Search for more papers by this authorCorresponding Author
Ming-Qiang Zhou
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan, 610041 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorCorresponding Author
Yong You
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorCorresponding Author
Wei-Cheng Yuan
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, Sichuan, 610106 China
E-mail: [email protected] (W.-C. Yuan); [email protected] (Y. You); [email protected] (M.-Q. Zhou)Search for more papers by this authorComprehensive Summary
The asymmetric cycloaddition reactions of 1,3-fused cyclic azomethine ylides have been extensively studied, but the non-cyclic α-functionalization of these compounds remains unexplored. Herein, an efficient combination of the catalytic enantioselective non-cyclic α-functionalization of 1,3-fused cyclic azomethine ylides and the remote-controlled asymmetric desymmetrization of N-arylmaleimides and cyclopentene-1,3-diones has been achieved with a catalyst system consisting of a chiral P,N-ferrocene ligand and AgNO2. This reaction allowed for the synthesis of a series of enantioenriched 3,4-dihydroisoquinoline derivatives bearing multiple stereogenic elements/centers with good yields and stereoselectivities. The practicality of this method was demonstrated by gram-scale synthesis and derivatizations of the products.
Supporting Information
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