对映选择合成
化学
烷基化
有机催化
电化学
有机化学
组合化学
催化作用
电极
物理化学
作者
Jin-Yu He,Na‐Na Wang,Ruinan Zhao,Ling-Xuan Kong,Cuiju Zhu,Tian‐Sheng Mei,Hao Xu
标识
DOI:10.1002/ejoc.202400817
摘要
Acridine scaffolds are present in biological and pharmaceutical molecules. However, achieving asymmetric functionalization of acridines remains challenging without an efficient and highly stereoselective approach. Here we demonstrate a facile electrooxidative asymmetric dehydrogenative coupling reaction of 9,10‐dihydroacridines with aldehydes. This method offers a sustainable and effective route to various chiral α‐alkylation of 9,10‐dihydroacridines in high yields with excellent enantioselectivities facilitated by readily available aminocatalyst. Detailed mechanistic studies and cyclic voltammetric analyses reveal that this asymmetric electrochemical reaction proceeds through redox‐mediated oxidation, followed by a nucleophilic attack with concurrently generated enamine. We anticipate that our research will open avenues for promising exploration in organocatalyzed electrochemical enantioselective transformations.
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