The Synthesis Of Aziridine Alcohol Chiral Ligands And The Applications In Asymmetric Catalytic Reaction

In this thesis, a series of aziridine alcohol chiral ligands were synthesized from L-serine. Then the catalytic efficiency and asymmetric induction of ligands for the Cu-catalyzed asymmetric Henry reaction and the asymmetric arylation reactions of aromatic aldehyde were studied in the presence of catalytic mounts of the chiral ligand.1. The design and synthesis of aziridine alcohol chiral ligandsA series of aziridine alcohol chiral ligands6a-e,10a-b,14a-b were synthesized from cheap and readily available L-serine1by means of esterification, condensation, reductive amination and ringclosure, then reaction with Grignard reagent. All16novel compounds were prepared. The structure of the products were confirmed by IR,’H NMR,13C NMR and HRMS. 2. The application of aziridine alcohol chiral ligands for asymmetric notro-aldol reactionIn the Cu-catalyzed asymmetric Henry reaction, we investigated the factors which influence the reaction including solvent, reaction temperature, additive and the amount of ligands to determine the optimal reaction conditions with chiral ligand6a. Then all the ligands were used as catalyst to promote the Cu-catalyzed asymmetric Henry reaction. After screening the optimal ligand and reaction conditions, we expanded the substrates of aromatic aldehyde and all of them can got good yields and enantioselectivity.3. The application of aziridine alcohol chiral ligands for asymmetric arylation reactionIn the asymmetric arylation reaction to benzaldehyde with p-tolylboronic acid, we studied the asymmetric catalytic effect of chiral ligands6a and15. Through investigated the factors which influence the reaction include the amount of ligands, the reaction temperature and zinc salt, we determined the optimal reaction conditions. The experimental results show that the catalytic effect of chiral ligand15is a little better than6a. In the optimal ligand and reaction conditions, we expanded the substrates of aromatic aldehyde and the reaction was best achieved97.2%of the yield and Ee Value up to95.3％.