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Ni(0)-Catalyzed Synthesis of Polycyclic α,β-Unsaturated γ-Lactams via Intramolecular Carbonylative Cycloaddition of Yne-imines with CO
Synlett ( IF 1.7 ) Pub Date : 2020-10-08 , DOI: 10.1055/s-0040-1707308
Sensuke Ogoshi , Keita Ashida , Yoichi Hoshimoto

A Ni(0)-catalyzed intramolecular carbonylative cycloaddition between 1,5-yne-imines and carbon monoxide (CO) is disclosed. When Ni(CO)3PCy3 was employed as a pre-catalyst, a variety of polycyclic α,β-unsaturated γ-lactams were prepared in up to 78% yield with 100% atom efficiency. Aza-nickelacycles, generated by the oxidative cyclization of yne-imines on the Ni(0) center, were experimentally confirmed as key intermediates. Moreover, diastereoselective transformations of the obtained products to afford highly substituted polycyclic γ-lactams with three contiguous carbon stereocenters are reported.

中文翻译:

Ni(0)-催化合成多环α,β-不饱和γ-内酰胺通过炔亚胺与CO的分子内羰基化环加成

公开了Ni(0)-催化的1,5-炔-亚胺和一氧化碳(CO)之间的分子内羰基化环加成。当 Ni(CO)3PCy3 用作预催化剂时,可以以高达 78% 的产率和 100% 的原子效率制备多种多环 α,β-不饱和 γ-内酰胺。由炔亚胺在 Ni(0) 中心氧化环化产生的氮杂镍环被实验证实为关键中间体。此外,还报道了所得产物的非对映选择性转化,以提供具有三个连续碳立体中心的高度取代的多环 γ-内酰胺。
更新日期:2020-10-08
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