化学
邻苯二甲酰亚胺
衍生化
胺化
区域选择性
组合化学
原子经济
磷化氢
分子
催化作用
有机化学
高效液相色谱法
作者
Kui Liu,Shao-Jie Cheng,Gen Luo,Zhishi Ye
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-11-15
卷期号:23 (23): 9309-9314
被引量:5
标识
DOI:10.1021/acs.orglett.1c03687
摘要
A novel and facile approach to synthesis of 1-substituted cyclopropylamines via phosphine-catalyzed formal tertiary Csp3-H amination of cyclopropanes was described. The indoles, pyrroles, imidazoles, uracils, 2-pyridone, pyrimidin-4(3H)-one, and phthalimide had been proven as good aminating partners. The present protocol features transition-metal-free, excellent regioselectivity, high-atom-economy, and mild reaction conditions and a broad range of substrates. The practicability of this protocol can also be demonstrated with late-stage modification of bioactive molecules, scaled up reaction, and divergent derivatization. Notably, the method has been used in the formal synthesis of the hormone-sensitive lipase (HSL) inhibitor. The mechanistic aspects were elucidated by both experimental and computational studies.
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