Asymmetric Construction Of Indole Derivatives And Cyclic Ketones Mediated By Magnesium Catalysis

Using catalytic asymmetric reactions to construct key frameworks of natural products is a highly attractive research area.The indole scaffold is a key motif of a number of alkaloids,so it is important to construct chiral indole derivatives.In this dissertation,some representative chrial indole derivatives have been synthesized by our designing reactions catalyzed by magnesium catalysts.This dissertation includes seven chapters.The first chapter included the introduction of synthetic strategies of some representative indole scaffold compound and related catalytic systems.In the second chapter,we synthesized pyrroloindolines by[3+2]-cycloaddition reaction of aziridines and C3-substituted indoles catalyzed by Mg Bu₂,after the exploration we choosed commercially available quinine as chiral ligand and N,O-bidentate compound as achiral additive.In the third chapter,we constructed chiral 3-alkyl-3-aryl oxindole structural motif employing aziridines and 3-aryl oxindoles by magnesium catalyst.In the fourth chapter,we achieved enantioselective formal[3+3]-cycloaddition reactions of 3-isothiocyanato oxindoles and aziridines,and we also tried to apply the enanentioriched ring-opening product in modification of peptides and organocatalyst.In the fifth chapter,we developed an asymmetric[3+2]-cyclization reactions of 3-isothiocyanato oxindoles and alkynyl ketones via an in-situ generated magnesium catalyst and obtained a series of chiral spirooxindoles in high yield and enantioselectivity.Based on the former section,in the sixth chapter,we tried the dearomatization of?-naphthols with chiral magnesium catalyst.By exploring of a series of oxazoline-OH chiral ligands reported during our previous work,the highly enantioselective dearomatization reaction could be realized and provided some chiral cyclic ketones.The last section is the summary of the asymmetric construction of indole derivatives and cyclic ketones mediated by magnesium catalysis.