重氮苯乙酸甲酯与烯胺的新型加成反应研究

Study on Novel Addition Reaction of Methyl Phenyldiazoacetate to Enamine

在铜盐催化下,苯乙酮衍生的烯胺与重氮苯乙酸甲酯(1)发生一种新型加成反应。该反应并不产生预期的环丙烷化合物,而是以较高的收率产生γ-酮酯化合物——4-氧代-2,4-二苯基丁酸甲酯。实验结果表明环状的和脂肪族的二级胺形成的烯胺都能与1发生加成反应,其中吗啉衍生的烯胺参与加成反应的产率最高。

A novel addition reaction of methyl phenyldiazoacetate to enamine （which was prepared from aeetophenone and secondary amine） was investigated using copper salt as a catalyst. A γ-ketoester, methyl 4-oxo-2,4-diphenylbutanoate（3）, was produced in good yield by the addition reaction, and none of the expected aminoeyclopropane product was found. The experament results show that both cyclic and acyclic secondary amines can be used for the addition reaction to obtain variable yields of 3, and morpholine derived amine affords best chemical yield.