Chiral Phosphoric Acid-Catalyzed Asymmetric Reactions Involving Isatins And 2-Vinylindoles For The Synthesis Of Enantiopure Indole Derivatives

This dissertation is divided into four parts.In the first part,we summarized a series of catalytic asymmetric reactions for constructing indole derivatives which were accomplished by the chemists from all over the world.Meanwhile,we introduced the background and research contents of this dissertation.In the second part,we mainly introduced the first catalytic asymmetric construction of the spirooxindole scaffold incorporated with a benzodiazepine moiety via chiral phosphoric acid-catalyzed three-component domino reactions of isatins,1,2-phenylenediamines and cyclohexane-1,3-diones,which afforded structurally complex spirobenzodiazepine oxindoles.This strategy not only provided an easy access to enantioenriched spirobenzodiazepine oxindoles with potential bioactivity,but also greatly enriched the research contents of catalytic asymmetric domino and multi-component reactions.In the third part,we reported the chiral phosphoric acid-catalyzed asymmetric Diels-Alder reactions of 2-vinylindoles with methyleneindolinones,which efficiently constructed the chiral spiro[tetrahydrocarbazole-3,3′-oxindole] architecture in high yields and excellent stereoselectivities,also,offered a collection of promising compounds with structural diversity for bioassay.This reaction not only provided an efficient strategy to access this scaffold based on hydrogen-bonding activation mode,but also supplied successful examples of catalytic asymmetric Diels-Alder reactions for constructing complex spiro-frameworks with optical purity.In the fourth part,we introduced a catalytic asymmetric dearomatization of 3-methyl-2-vinylindoles by using quinone monoimides as suitable electrophiles in the presence of chiral phosphoric acid.In this part,we successfully switched the reactivity of the two reactive positions of vinylindoles and enriched the chemistry of catalytic asymmetric dearomatization.