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 , Jian-Mei Wang , Yan-Ping Zhang , Zhen-Hua Wang , Lei Yang , Jian-Qiang Zhao , Ming-Qiang Zhou , Yong You , Wei-Cheng Yuan
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (16) : 2029 -2035.
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
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.
Asymmetric catalysis / Desymmetrization / Cyclic azomethine ylides / N-Arylmaleimides / Cyclopentene-1,3-diones
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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