Study On Organocatalvtic Michael Addition Reactions

In recent years, small molecule organocamine catalytic asymmetric synthesis have made tremendous progress. It has become a new field of asymmetric catalysis research. Asymmetric Michael addition reaction is important. This article inspects the various affecting factors about primary amine catalysts for asymmetric Michael addition reaction process.First of all, we made organic nitrostyrene catalyzed asymmetric thia Michael addition reaction as a model. By deeply studying on various factors of the asymmetric Michael addition reaction, we discussed influencing factor on the Michael reaction,such as the different types of organic amine catalyst, solvents, additives, temperature and so on, through extensive research, we concluded that the best conditions of the organic nitrostyrene catalyzed asymmetric thia-Michael addition reaction was as follows:under temperature0℃,(S)-QN-NH-Ts as the catalyst,1,4-dioxane as the solvent, the mol raw material feeding reaction nitrostyrene: thio-acetic acid=1:2, feeding methods using slow addition techniques.We made organic catalytic reaction of β-naphthol with nitrostyrene as another model, continuing to study the asymmetric Michael reaction. By studying we found that optimal catalyst and solvent of organic catalytic beta-naphthol reaction with nitrostyrene were Ts-diaminocyclohexane and toluene。Then, we have also done some research about the factor of Biginelli reaction. We have developed a new dual metal catalytic system. Through the research we found that, in all factors we have done, he best condition is:QN-NH2(10mol%) as the catalyst, NbCl5(10mol%) and CeCl3(5mol%) as the jont catalyst,1,4-dioxane as the solvent, at room temperature for48h. Under this complex condition, benzaldehyde, urea and ethyl acetoacetate operated the Biginelli reaction,wo got a result of76%yield and69%ee.In the process of experimental work, we also synthesized several chiral thiourea-amine catalyst of small organic molecules, which expanded the scope of the study of the chiral catalytic Michael addition reaction, and have got a certain catalytic effect.