Organocatalytic Asymmetric Tandem Reaction And Substitution Reaction Of Indole Derivatives

In the first chapter,we depicted the background on organocatalytic asymmetric tandem reactions and substitution reactions of indole derivatives such as isatins,tryptophols and 2-indolylmethanols.In addition,the target and the contents of this paper were also described.In the second chapter,we set up an organocatalytic asymmetric [4 + 2] tandem reaction of isatins.In the presence of chiral thiourea-tertiaryamine catalyts,the tandem reaction of isatins with enolizable anhydride has been developed for the ennantioselective construction of dihydroisocoumarin-based spirooxindole frameworks in high yields,excellent diastereo-and enantioselectivities(up to 99%,all >95:5 dr,up to 99% ee).In the third chapter,we established an organocatalytic asymmetric C2-nucleophilic substitution reaction of tryptophols.In the presence of chiral phosphoric acid,the catalytic asymmetric C2-nucleophilic substitution of tryptophols with ortho-hydroxybenzyl alcohols has been established,leading to the generation of triarylmethane products in generally high yields and excellent enantioselectivities.This reaction will enrich the research contents of catalytic asymmetric reactions of tryptophols.More importantly,this reaction will not only provide a protocol for constructing enantioenriched triarylmethane frameworks,but also open an avenue for finding new catalytic asymmetric transformations of tryptophols.In the fourth chapter,we established an organocatalytic asymmetric tandem reaction of 3-vinyl-substituted 2-indolylmethanols.in the presence of chiral phosphoric acid,the catalytic asymmetric tandem cyclization of 3-vinyl-substituted 2-indolymethanols with 2-naphthols has been established,which constructed chiral cyclopenta[b]indole frameworks in generally high diastereoselectivity and enantioselectivity.This reaction not only provides an easy access to chiral cyclopenta[b]indole scaffolds,but also advances the chemistry of indolylmethanols,especially catalytic asymmetric transformations of indolylmethanols.