甲基吖内酯与原位亚胺的不对称催化反应的研究

Asymmetric Catalytic Reactions Study of Methyl Azlactone and in Situ the of the imine

通过对前人文献调阅发现对苯磺酰吲哚在碱性条件会在原位产生烯亚胺具有良好的亲电性并且甲基吖内酯在辛可宁硫脲催化会脱氢质子具有亲核性。因此通过辛可宁硫脲催化下苯磺酰吲哚与甲基吖内酯就可能发生对应选择性的迈克加成反应。我们通过吖内酯与苯磺酰吲哚不对称催化反应制备得到化合物3。改变苯磺酰吲哚上的R取代基团从而制得各种相应的化合物3。通过对制备的化合物3进行核磁共振碳谱、核磁共振氢谱、液相色谱、比旋光度、高分辨质谱等理化参数的测定,得出甲基吖内酯与苯磺酰吲哚在催化剂辛可宁硫脲催化作用下得到好的产率和高纯度的光学活性的产物。

lmine Intermediates Generated in situ from Arylsulfonyl Indoles possess good elcctrophilicity and methyl azlactone catalyzed by cinchonine thiourea have nucleophilicity by the previous literature sources. So, Highly enantioselective Michael Addition reaction of benzenesulfonyl indole to methyl azlactone catalyzed by cinchonine canoccur the azlactone and henzenesulronyl indole was prepared according to the reported literature, and The experiment required solvent was purified according to standard. The catalytic asymmetric reaction of compound 3 was prepared by Azlactone and benzenesulfonvl indole. Changing the R-benzenesulfonyl indole substituent groups may manufacture a variety of corresponding compound 3. Through a variety of instruments and analysis of compound 3, the NMR 13C NMR, 1H NMR, liquid chromatography, high-resolution mass spectrometry and other physical and chemical parameters,we can see the compound 3 in good yield and the high optical activity.