The Research Of The Method Of C-3 Chiral Quaternary Center Of Oxindole

Heterocyclic molecules containing indole skeleton widely present in natural products.Of which,3-substituted-2-oxindole caused great concerns of chemists.That's because this basic skeleton composed of the basic components of new drug ingredients.Therefore,building oxindole C-3 chiral quaternary carbon center has become a hot research field of organic synthesis.We have developed organic catalysis method to synthesize functional group substituted oxindoles.This thesis is divided into three chapters.The first chapter is about the bioactive of C-3 chiral quaternary carbon oxoindole and C-3 chiral quaternary carbon oxoindole synthesis related to this article summarizes aspects of the development process.The first chapter can be divided into two parts:isatin is used as a substrate to get C-3 chiral quaternary carbon oxoindole in the first part,and a number of C-3 chiral quaternary carbon oxoindole was given by isatin is cited in this part.3-halogenated oxoindole as substrate to obtain C-3 chiral quaternary carbon oxoindole is in the second part.Many of the previous work is to connect the nucleophile with the catalyst to control the a chiral center.However,in this section we can see that our work is incorporated electrophilicity of 3-halogenated oxoindole with the catalyst to give an intermediate indol-2-one to control the generation of a chiral center.This can largely expand the chiral oxoindole skeleton synthetic diversity,thus providing a broader method for the asymmetric synthesis of natural products or drug molecules.In the second chapter,we construct chiral 3-hydroxy-3-methyl-nitro-2-oxindole by an organic asymmetric catalysis Henry reaction to obtained total synthesis of(S)-(-)Spirobrassinin.In the third chapter,we use organic catalytic oxidation of phenol and 3-bromo-oxindole reaction to construct C-O chiral quaternary carbon center.This method is incorporated electrophilicity of 3-halogenated oxoindole with the catalyst to give an intermediate indol-2-one to control the generation of a chiral center.