The Study On The Asymmetric Addition Reaction Of Zinc Diethyl With Aromatic Aldehyde Catalyzed By Optically Active γ-amino Alcohol

Optically active secondary alcohol is an important intermediate in the synthesis of many natural products, optically active materials and drugs. Meanwhile, the asymmetric addition of organic metallic reagents with aldehydes is a significant approach in theconstruction of C - C bond and production of optically active secondary alcohols.In this dissertation, we have synthesized a series of chiral y -amino alcohol ligands from L- Prolinol as start material, optimized the synthetic methods and conditions, and then used them to catalyze the asymmetry reaction of Zinc Diethyl with Aromatic Aldehyde. By optimization those ligands, we have founded that good catalytic reactivity and selectivity were obtained when used chiral ligand 83b to catalyze the reaction. We also investigated the influence of reaction temperature, solvents, catalyst amount and additives on the reactivity and enantioselectivity. And found that when the reaction temperature was -10℃, m-hexane and toluene was 1:1(v/v) as solvent and the catalyst load is 10%, good results were obtained. With the optimal conditions, we studied the adaptability of the catalyst system to substrates, and applied it to catalyze the addition reaction of Zinc Diethyl with a series Aromatic Aldehydes and obtained 15 - 89% yields and 18 - 81 % e.e. value.