化学
动力学分辨率
产量(工程)
亲核细胞
催化作用
前药
吡啶
芳基
组合化学
氧化物
动能
有机化学
对映选择合成
热力学
生物化学
物理
烷基
量子力学
作者
Yang-Guang Chen,Hong‐Jie Yu,Tian Yin,Cheng Peng,Ming‐Sheng Xie,Hai‐Ming Guo
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-07-20
卷期号:25 (30): 5585-5590
被引量:2
标识
DOI:10.1021/acs.orglett.3c01915
摘要
A chiral 4-aryl-pyridine-N-oxide nucleophilic organocatalyst was used to synthesize chiral phthalidyl ester prodrugs by the acylative dynamic kinetic resolution process. By using the 3,5-dimethylphenyl-derived ArPNO catalyst, the phthalidyl esters were obtained in up to 97% yield with 97% ee at room temperature. Two phthalidyl esters of prodrugs, talosalate and talmetacin, were generated. By control experiments and density functional theory calculations, an acyl transfer mechanism was proposed.
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