化学
苯乙炔
立体选择性
化学位移
计算化学
铜
反应条件
组合化学
有机化学
催化作用
物理化学
作者
Cristina Cimarelli,Corrado Bacchiocchi,Manuel Petroselli,Martina Lippolis,Dario Gentili,Serena Gabrielli
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2022-11-30
摘要
Abstract The stereoselective synthesis of several secondary propargylamines by the copper-promoted A3-coupling reaction of aliphatic and aromatic aldehydes with phenylacetylene and (R)-(+)-phenylethylamine is here reported. Two different synthetic methodologies have been investigated in this study, involving CuSO4/NaI and CeCl3·7H2O/CuI promoting systems. The reported methodologies were compared in terms of efficiency, diastereoselectivity, and toxicity, both showing advantages with respect to the current methodologies. The relative configurations of each of the obtained propargylamines, previously unknown in the literature, were assigned by comparison of the 1H NMR experimental chemical shifts with those theoretically predicted via the DFT-GIAO method.
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