School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, China.
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.
Org Lett. 2020 Nov 6;22(21):8326-8331. doi: 10.1021/acs.orglett.0c02963. Epub 2020 Oct 12.
Herein, a selective tandem C-C bond-forming reaction with CO was developed to realize the bridging of enaminones and synthesis of 1,4-dihydropyridines, respectively. -Butylamine significantly promoted this CO deoxymethylenation procedure catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and ZnCl. The mechanism involving the formation of bis(silyl)acetal, nucleophilic addition, and amine elimination was also interpreted to clarify the bridging of two molecules of enaminones with CO and the generation of dihydropyridine derivatives.
本文开发了一种选择性的串联 C-C 键形成反应与 CO,分别实现了烯胺酮的桥接和 1,4-二氢吡啶的合成。-丁胺显著促进了 1,5,7-三氮杂双环[4.4.0]癸-5-烯(TBD)和 ZnCl 催化的 CO 去甲叉反应。还解释了涉及双(硅基)缩醛形成、亲核加成和胺消除的反应机制,以阐明烯胺酮与 CO 的两个分子的桥接以及二氢吡啶衍生物的生成。