Trapping of Transient Zwitterionic Intermediates by N-Acylpyridinium Salts: A Palladium-Catalyzed Diastereoselective Three-Component Reaction

被引：11
|
作者：
Zhang, Dan [1 ]
Kang, Zhenghui [1 ]
Hu, Wenhao [1 ]
机构：
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 11期
关键词：
PYRIDINE; DERIVATIVES; ARYLATION; PYRROLE; OXIDES; DIAZOACETAMIDES; SUBSTITUTION; ALKYLATION; GRIGNARD;
D O I：
10.1021/acs.joc.7b00560
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We developed a palladium-catalyzed diastereoselective three-component reaction of N-aryl diazoamides, pyridine, and chloroformate, which proceeded through trapping of transient zwitterionic intermediates by in situ formed N-acylpyridinium salts in a regioselective 1,4-addition fashion. This reaction can rapidly provide a library of biologically relevant 4-(2-oxoindolin-3-y1)-1,4-dihydropyridine derivatives in high yields (up to 98%) with moderate to excellent diastereoselectivities (up to >95:5 dr) under mild reaction conditions.
引用
收藏
页码：5952 / 5958
页数：7
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