Asymmetric Cycloaddition Reactions Catalyzed By Bipyrrolidine Derived Tetradentate Iron Complexes

To fit the ever-growing needs on sustainable development and green chemistry,eco-friendly iron catalysts to achieve asymmetric reactions and obtain chiral products with high stereoselectivity has been a problem of concern to many chemical workers.In this thesis,we investigated the cycloaddition reaction catalyzed by the chiral Fe-BPsalan complexes withα,β-unsaturated carbonyl compounds derivatives based on N-methyl imidazole and phthalimide react with cyclopentadiene,respectively.Through the selection and optimization of the conditions:when the substrate is 2-cinnamyl-N-methyl imidazole only 5 mol%chiral Fe-BPsalan complex catalyst is required,add silver tetrafluoroborate,and solvent of THF at 25 ^oC for 8 h,the chiral target product was obtained with 94%yield and 98%enantioselectivity（23 examples）;When the substrate is2-cinnamoylisoindoline-1,3-dione need 5 mol%chiral Fe-BPsalan complex was added as catalyst,add silver perchlorate,5?MS as additive,and solvent of DCE at 25 ^oC for 5 h,the chiral target product was obtained with 95%yield and 90%enantioselectivity（13 examples）.Using the same chiral catalyst framework,the three dimensional structures of the chiral products obtained from the two substrates are different.For different aryl or alkyl substitutedα,β-unsaturated carbonyl derivatives based on N-methyl imidazole and phthalimide,good performances on cycloaddition were shown.And the standard substrate of 2-cinnamyl-N-methyl imidazole was amplified to gram scale,the reaction product can be obtained with 90%yield and 98%enantioselectivity.