Trifunctionalization Reaction with Pyrazoleamide Rh Carbenes
Maoqing Shi , Pei Li , Haohan Zheng , Siyu Wu , Xiaoyan Yang , Zhonghui Zhang , Rui Jiang , Wenhao Hu , Yu Qian
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) : 3414 -3420.
Multifunctionalization reactions involving reactive intermediates offer powerful strategies for the rapid construction of complex molecules. Herein, we describe two trifunctionalization reactions of pyrazoleamide-derived metal carbenes. Both transformations are proposed to proceed through a zwitterionic intermediate, formed via nucleophilic attack and pyrazole migration, followed by electrophilic trapping. This approach enables the efficient synthesis of 3-hydroxy-2-oxindole derivatives from isatins and amines in good yields, as well as chiral β-aminoamide derivatives via a Rh/CPA co-catalytic system with excellent enantioselectivity. Importantly, both classes of compounds exhibited significant inhibitory activity against multiple tumor cell lines.
Metal carbenes / Trifunctionalization / 3-Hydroxy-2-oxidized indole / β-Aminoamide derivatives / Zwitterions / Diazo compounds / Ylides
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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