Asymmetric Synthesis Of Chloroaziridine And Dichloroamine Compounds

Amines are present in a number of drugs and drug candidates.The asymmetric synthesis of amines is becoming more and more popular,and represents an extremely important endeavor in the discovery and production of new pharmaceutical agents.Meanwhile,the asymmetric synthesis based upon chiral tert-butylsulfinamide becomes one of the useful synthetic methods of amines gradually,and the tert-butylsulfinamide is increasingly being applied in many research areas.Aziridine is the smallest nitrogen-bearing heterocyclic compound and an important intermediate in organic synthesis.Introducing halogen atomo to aziridine could increase the reaction sites,that are important to the synthesis of more nitrogenous compounds.Therefore,the synthesis of halogen substituted aziridines is always a hot research topic in the field of organic synthesis.Previous reports on the synthesis of halogen substituted aziridines are limited,and the synthesis methods couldn't be widely applied.Based on previous synthesis of halogen substituted aziridines,we developed a new method for the synthesis of chlorine substituted aziridines and dichloromethyl amines.This thesis includs three chapters.Recent advances in the synthesis and application of tert-butylsulfinamide,tert-butylsulfinamide imines,halogen substituted aziridines and dichloromethyl amines are summarized in Chapter one.The new synthetic method of chlorine substituted aziridines and dichloromethyl amines is introduced in Chapter two.By screening and optomizing reaction conditons,such as solvents,temperatures,and bases,we successfully developed a highly efficient and practical method for the asymmetric synthesis of chlorine substituted aziridines and dichloromethyl amines.The new process is based on the formation of dichloromethyl anion which is formed from dichloromethane,follows by the nucleophilic dichloro-methylation of chiral N-(tert-butylsulfinyl)imines.Moreover,the application of this strategy was studied,and a number of chlorine substituted aziridines and dichloromethyl amines with different substitued groups were synthesized.Experiment procedures,physical datas and spectral datas of all compounds are recorded in Chapter three.