Study Of Catalytic Asymmetric Michael Addition Reaction Of Aldehydes To α-substituent Nitroolefins

In this dissertation, a series of bifunctional catalysts with sulfonamides and thiourea structure unit were designed and synthesized from proline and hydroxyproline. A series of a-substituent nitroolefins were synthesized also, and then, these bifunctional catalysts were evaluated in the asymmetric Michael addition reaction of aldehydes with a-substituent nitroolefins and it was demonstrated that the 2-trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether catalyst 29 derived from hydroxyproline with good catalytic efficiency. After investigating the influence of solvent, reactive temperature, catalyst load and additive on the reactive activity and selectivity, resulted in the optimal reactive conditions as the reactive temperature was 0℃, DMF as solvent,5 mol% p-nitrobenzoic acid as additive and 5 mol% catalyst load was used. When the asymmetric Michael addition reaction proceeded under the optimal conditions,>80% yield, up to 95% ee and 19:1 d.r. could be obtained.