The Synthesis Of Jacobsen Catalyst And Applications In The Asymmetric Synthesis

Salen metal catalysts,especially Jacobsen catalyst,have been widely used in catalytic symmetric reaction, such as asymmetric epoxidizing reaction of Olefine, hydrolytic kinetic resolution of meso epoxides, Strecker reaction, asymmetric cyanide silane, asymmetric ring opening of racemic terminal epoxides, racemic epoxides open-loop asymmetric reactions, the Diels-Alder cycloaddition, asymmetric cyclopropanation, and so on.This thesis consists of three parts:(1) Synthesis of Jacobsen catalyst. (R,R)-1, 2-diammoniumcyclohexane mono-(+)- tartrate salt and (S,S)-1, 2-diammoniumcyclohexane mono-(+)-tartrate are acquired through the resolution of cis/trans-1, 2-diammoniumcyclohexane, and react with 3, 5- Di-tert- butyl-2- Hydroxybensaldehyde and get Jacobsen catalyst in the end. Their structures are characterized by UV, IR, 1H NMR, 13C NMR.(2) Hydrolytic kinetic resolution of epihalohydrin. Systematic study of reaction temperature, time, concentrations of catalyst, and recycle times of catalyst on how to affect the yield and optical purity of production. This research can be provided a reliable basis for industrial production.(3) Synthesis of PLC. PLC is synthesized by amination, cyanidation, hydrolytic action and esterification with S- epihalohydrin as starting material, and identified by IR, MS, NMR as well as element analysis. This process has the advantages of mild conditions, convenient operations, besides low cost.