Study On Chiral Primary Amine Catalyzed Asymmetric Mannich Reaction Of Acetaldehyde With Cyclic Trifluoromethyl Ketimines

Many anti-HIV drugs bear a chiral trifluoromethyl quaternary center moiety.Accordingly,efficient approaches to valuable chiral molecular architectures with chiral trifluoromethyl quaternary center are of considerable synthetic and pharmaceutical importance.In addition,chemical scientists have made great progress,which utilizing acetaldehyde as synthon conversion structure to form C-C bonds in asymmetric synthesis research.The primary amine catalysts have attracted enough attention,but there are still some works deserve scientists' further research.This thesis screened proline,prolinol,prolinol silyl ethers,thiourea,cinchona and chiral bifunctional amine catalyst.It was the first time that utilizing chiral bifunctional primary primary amine catalyst to catalyze the asymmetric Mannich of aldehyde with.cyclic trifluoromethyl ketimine.We screened the optimal reaction condition that utilizing 20mol%chiral bifunctional amine catalyst with TfbH in 2:1 ratio,tetrahydrofuran,20mol%o-nitrobenzoic acid as additive,reacting at room temperature for 16 hours.A series of trifluoromethyl quaternary center moiety had been sythesised,we obtained better yield(up to 90%)and enantioselectivity(up to 95%).We optimized the condition of synthesis cyclic trifluoromethyl ketimine,then we the explored the function of chiral bifunctional primary amine catalysts and the reaction mechannism.Finally,the method of universality of had been explored.Though we had not got the perfect results,it still provided valuable experience for the researchers who continues the work...