Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.
J Org Chem. 2017 Jun 2;82(11):5952-5958. doi: 10.1021/acs.joc.7b00560. Epub 2017 May 19.
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-yl)-1,4-dihydropyridine derivatives in high yields (up to 98%) with moderate to excellent diastereoselectivities (up to >95:5 dr) under mild reaction conditions.
我们开发了一种钯催化的 N-芳基重氮酰胺、吡啶和氯甲酸酯的非对映选择性三组分反应，该反应通过在区域选择性 1,4-加成方式中通过原位形成的 N-酰基吡啶鎓盐捕获瞬态两性离子中间体进行。在温和的反应条件下，该反应可以快速提供一系列具有生物相关性的 4-(2-氧代吲哚啉-3-基)-1,4-二氢吡啶衍生物库，产率高达 98%，非对映选择性适中至优异（高达 >95:5 dr）。
