Studies On The Synthesis And Asymmetric Catalytic Properties Of The Polymer-Supported Chiral Catalysts

Polymer-supported chiral catalysts have many merits which are easily removed at the end of the reaction and can possibly be re-used and overcome these problems such as the high cost and difficulty in reusability of homogeneous catalysts. Adapt to the need of green chemical industry and sustainable development. In this paper, the application and development of polymer-supported chiral catalysts in asymmetric reaction were reviewed; kinds of new polymer-supported chiral catalysts were synthesized and characterized and the application of polymer-supported chiral catalysts in the asymmetric dihydroxylation reaction and the asymmetric reduction reaction of prochiral ketone was discussed. The thesis consists of three parts as follows.Part I : ReviewCinchona alkaloid catalysts, asymmetric catalyze, the application and recent development of polymer-supported cinchona alkaloid catalysts in asymmetric dihydroxylation reaction, the alkylation of active methylene group, asymmetric reduction reaction of prochiral ketone and asymmetric synthesis of chiral epoxides by catalyzing alkenes were reviewed. As a kind of newly catalysts, their prospect and the problems they faced were also discussed in this part.Part II: The synthesis and the characterizing of the PAA-supported chiral quaternary ammonium salts catalysts and the study on its catalytic propertiesThe part consists of two subsections. The PAA-supported chiral quaternary ammonium salts catalysts were synthesized by the stuff (cinchonine or BCIP). Their structures were characterized by means of FT-IR, elemental analysis, XPS; the chiral quaternary ammonium salts were first used as catalysts for the dihydroxylation of olefins. Their catalytic properties for the AD processes were investigated. The comparison of the products e.e., the conversion of the substrate among different AD processes was employed with determined by HPLC. The effects of the time, the temperature, the ratio of catalyst to substrate as well as the recycle times were also discussed. It is demonstrated that the chiral quaternary ammonium salts catalysts exhibit promising catalytic properties for the substrate.Part III: The synthesis and the characterizing of the macroporous aminomethyl resin-supported cinchona alkaloid complexes and the study on its catalytic propertiesThe part consists of two subsections. the macroporous aminomethyl resin -supported cinchona alkaloid complexes were synthesized by the stuff (cinchonine, quinine and macroporous aminomethyl resin). Their structures were characterized by means of elemental analysis, XPS, TG/DTA; the chiral polymer-supported complexes were first used as catalysts for the reduction of ketones. Their catalytic properties for the reduction processes were investigated. The comparison of the products e.e., the conversion of the substrate among different reduction processes was employed with determined by HPLC. The effects of the time, the temperature, the ratio of catalyst to substrate, reaction solvent as well as the recycle times were also discussed. It is demonstrated that the recovered catalyst can be reused without appreciable loss of activity.