Lewis Acid Catalyzed Asymmetric Fluorination And Cvclization Reactions

Since the discovery of the fluorine substitution reaction,its application in organic synthesis is more and more extensive.This dissertation is mainly focus on the catalytically asymmetric aldol type reaction of fluorinated indan derivatives and isatins catalyzed by Lewis acid combined with chiral diamine ligands,providing the fluorinated 3-substituted Indolin-2-ones in good yields,moderated to good diastereo-and enantioselectivities.Furthermore,the[3+2]cycloaddition reaction of substituted aziridine and indoles were also studied.The main contents of this thesis are as follows:The first chapter introduce the common synyhesis methods of organic fluorinated compounds and its application in industry and medicinal chemistry.The development of catalytic asymmetric fluorination reaction catalyzed by organocatalysts and chiral metal complexes are also described in detail.In the second chapter,asymmetric aldol type reaction of fluorinated indan derivatives and isatins catalyzed by Lewis acid combined with chiral diamine ligands were investigated.Different reaction conditions such as Lewis acids,chiral ligands,solvents,additives et al were tested,and the desired product was obtained in good yield,diastereo-and enantioselectivity.After the optimization of reaction condition,e series of fluorinated indan derivatives and isatins were explored,and the fluorinated 3-substituted Indolin-2-ones in good yields,moderated to good diastereo-and enantioselectivities.At last,[3+2]cycloaddition reaction of substituted aziridine and indoles were carried out.From substituted indole substrate departure,Lewis acid Sc(OTf)3 can directly activate aziridination C-C bond to form a five-membered ring product,and achieve higher yield and moderate dr.