Research Report On Optimization Of Asymmetric Michael Addition Reaction Of Anthracene And Nitroene Catalysted By Organocatalysts

Objective:The development and application of chiral compounds are closely related to human life,health and production.For example,chiral drugs can avoid adverse drug reactions and improve curative effects;chiral pesticides can avoid environmental pollution;chiral stealth materials can eliminate or reduce Electromagnetic interference reduces electromagnetic pollution.Therefore,how to obtain chiral compounds efficiently has become a research hotspot of scientists.At present,asymmetric catalytic reaction is an excellent means to obtain chiral compounds,and the asymmetric Michael addition reaction catalyzed by small organic molecules is expensive,toxic and easy to residue.The metal,which has unique advantages in application,has attracted much attention.However,there are still some shortcomings in the asymmetric Michael addition reaction catalyzed by small organic molecules.Problems such as large amount of catalyst,long reaction time,poor catalytic effect and poor universality have yet to be further solved.Therefore,this paper hopes to explore the basic theory of asymmetric catalytic Michael addition reaction of organic catalyst by studying the optimization of organic catalytic asymmetric Michael addition reaction process,in order to improve the inadequacies of organic asymmetric catalytic Michael addition reaction and expand the type of catalyst.To obtain better stereoselectivity and broaden the range of substrates to provide a driving force for the scientific career of chiral compounds.Method:The catalytic performance of the catalyst was investigated by using the thiourea and prolinol derivative catalysts in the asymmetric Michael addition reaction of anthrone and nitroolefin.The solvent,temperature and catalyst dosage were investigated.Sexual effects,screen out the optimal reaction conditions and explore the scope of application of the substrate to investigate universality.Result:The optimum reaction conditions for the thiourea derivative organic catalyzed asymmetric Michael addition reaction scheme of anthrone and nitroolefin are:5 mol%catalyst 3f,chloroform as solvent and room temperature reaction.Asymmetric Michael addition reaction applied to 13 different substituted nitroolefins gave excellent yields(80-97%)and reaction stereoselectivity(86-99%ee).In the optimization scheme of the asymmetric Michael addition reaction of the indole alcohol derivative organic oxime and nitroolefin,the optimal reaction conditions were as follows:10 mol%catalyst 5b,toluene as solvent,and reaction at room temperature.Asymmetric Michael addition reaction applied to 10 different substituted nitroolefins gave excellent yield(88-99%)and moderate reaction stereoselectivity(46-66%ee).Conclusion:This paper expands the type of small organic catalysts suitable for asymmetric Michael addition reactions by analyzing and researching the optimization of asymmetric small Michael addition reaction of small organic molecules.The thiourea and prolinol catalysts are for the first time.It is applied to the asymmetric Michael addition reaction of anthrone and nitroolefin.The optimum reaction conditions of the selected thiourea catalyst 3f are good.The optimal reaction conditions for the screening of the proline-based catalyst 5b are still suitable.To improve,it provides an important theoretical basis for the development of chiral compound science and technology.