Synthesis And Catalytic Asymmetric Reaction Of Novel Chiral Camphor Schiff Base

With development of asymmetric synthesis,designing the novel chiral ligands with the simple structure and easily synthesis become more and more important,especially derivate from natural chiral compound.In the meantimes,mild reaction condition with high chemical and enantiomer selectivity also becomes another pursued target.The research work of this paper mainly includes the following four parts:1.The part of literature review.In this thesis,the research progress of chiral Schiff base in asymmetric field and asymmetric Friedel-Crafts alkylation reaction,the progress of synthesis chiral phosphoric acid compounds and chiral phthalide compounds were reviewed and evaluated.Based in the review,the research aim and significance of this thesis were derivation.2.The synthesis of chiral camphor ligands.In the second part,natural chiral D-camphor sulfonic were used as starting material to synthesize its Schiff base derivatives by several convenience steps,8 kinds of chiral D-camphor Schiff base derivatives were produced successfully.3.Asymmetric Friedel-Crafts alkylation reaction.Then,using the chiral D-camphor Schiff base derivatives cooperated with copper salt as catalysts in asymmetric Friedel-Crafts alkylation reaction with nitroolefin and pyrrole was explored.After screening and optimizing the reaction conditions,the Schiff base L2 of chiral D-camphor and CuBr complexes as catalysts,toluene as solvent and piperidine as additive at room temperature were given the best results.Nitroolifins with different substituents were also used in this process to give moderate enantioselectivity.4.Asymmetric Pudovik-Lactonization reaction.While,Schiff base of chiral D-camphor with ferric salt to catalyze asymmetric Pudovik-Lactonization reaction of methyl 2-formylbenzoate and diethyl phosphite were also explored.Different Schiff base and ferric salt were uesd to catalyst model reaction,Schiff base L4 and anhydrous FeCl2 was the best catalyst choice with THF as reaction solvent,anhydrous sodium carbonate as additive at room temperature based on the reaction results.Different 2-formylbenzoate and three dialkyl phosphite were using in this new catalytic process to produced good results.