Ni(0)-Catalyzed Synthesis of Polycyclic α,β-Unsaturated γ-Lactams via Intramolecular Carbonylative Cycloaddition of Yne-imines with CO

Ni(0)-Catalyzed Synthesis of Polycyclic α,β-Unsaturated γ-Lactams via Intramolecular Carbonylative Cycloaddition of Yne-imines with CO
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Ni(0)-催化炔亚胺与CO分子内羰基环加成合成多环α,β-不饱和γ-内酰胺

DOI:
10.1055/s-0040-1707308
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发表时间:
2020
期刊:
影响因子:
2
通讯作者:
Sensuke Ogoshi
Sensuke Ogoshi
中科院分区:
化学4区
文献类型:
--
作者:
Keita Ashida;Yoichi Hoshimoto;Sensuke Ogoshi

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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。以Ni(CO)_3PCy_3为预催化剂,以100%的原子效率合成了多环α,β-不饱和γ-内酰胺,产率高达78%。氮杂镍杂环化合物是通过炔亚胺在Ni(0)中心上的氧化环化反应生成的,实验证实其为关键中间体。此外,所获得的产品的非对映选择性转化,以提供高度取代的多环γ-内酰胺与三个连续的碳立体中心的报告。
A Ni(0)-catalyzed intramolecular carbonylative cycloaddition between 1,5-yne-imines and carbon monoxide (CO) is disclosed. When Ni(CO)3PCy3was 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.
1,5-炔亚胺上 N-芳基磺酰基的分子内迁移催化合成异喹啉
DOI: 10.1246/bcsj.20190301
发表时间: 2020
影响因子: 4
作者:
Hoshimoto Yoichi;Nishimura Chika;Sasaoka Yukari;Kumar Ravindra;Ogoshi Sensuke
通讯作者: Ogoshi Sensuke