X=Y-ZH compounds as potential 1,3-Dipoles. Part 281,2 the iminium ion route to azomethine ylides. background and reaction of amines with bifunctional ketones.
作者:Harriet Ardill、M.J.R. Dorrity、Ronald Grigg、Mooi-Sin Leon-Ling、J.F. Malone、Visuvanathar Sridharan、Sunit Thianpatanagul.
DOI:10.1016/s0040-4020(01)96013-2
日期:1990.1
The reaction of isatin, ninhydrin and acenaphthenequinone with primary and secondary amines gives rise to stereospecific formation of intermediate azomethine ylides which can be trapped by cycloaddition to methyl acrylate or N-methylmaleimide. The regiochemistry of the cycloadditions to methyl acrylate is controlled by both frontier orbital and steric interactions with the latter dominating in the
靛红,茚三酮和啶醌与伯胺和仲胺的反应引起中间体偶氮甲亚胺基立体定向形成,该中间体可通过环加成而被捕集到丙烯酸甲酯或N-甲基马来酰亚胺中。丙烯酸甲酯的环加成物的区域化学反应受前沿轨道和空间相互作用的控制,在所研究的实例中,后者占主导地位。