Chiral Phosphoric Acid Catalyzed [3+2] Cycloaddition Reaction Of Naphthalene Azo With 3-Vinyl-Indole

Vinyl indole is an important organic synthesis intermediate with high reactivity.The main types of reactions involved : [3+2] cycloaddition reaction,Michael addition reaction,[4+2] cycloaddition reaction(D-A reation)and so on.In recent years,its asymmetric synthesis reaction has long been a research hotspot for chemists.This paper is divided into three chapters:Chapter One: describes various types of reactions involving 2,3-position of indole and ethylene moiety of vinyl indole in recent years.Chapter two: describes the chiral phosphoric acid catalyzed [3+2] cycloaddition reaction of naphthalene azo compound with vinylindole compound.Enantioselectively enriched 2,3'-bisindole backbones derivative 3 or 3,3'-bisindole backbones 5 has been synthesized by changing the size of the substituent at the2-position of the substrate,adjusting the catalyst,solvent,and reaction time.Which were bearing two consecutive chiral centers were obtained respectively with above90% excellent yields and ee values.Additionally,a reasonable reaction mechanism has been proposed.Chapter three: describes our attempts on the center to axial charity conversion reaction,and 3,3'-bisindoles derivative 6 bearing a chiral axis were achieved successfullyby varying the oxidizing agent,solvent,reaction time and concentration conditions.The yields and the ee values of poroducts were as high as 90% or more,and the conversion cp is greater than 0.95.