Synthesis Of 3-Indolylglycine Derivatives Via Dinuclear Zinc Catalytic Asymmetric Friedel–Crafts Alkylation Reaction

Optically active 3-indolylglycine derivatives can be used as important synthetic intermediates and building blocks in natural and man-made products.Asymmetric catalysis provided the most significant and effective approach to prepare these compounds,since limited quantity chirality controlling element is used.In this thesis,a direct asymmetric Friedel–Crafts alkylation reaction between a wide range of indoles and ethyl 2-(4-methoxyphenylimino)acetate catalyzed by Trost's dinuclear complex is studied.A series of 3-indolylglycine derivatives were synthesized in enantioselectivity of up to > 99% ee using 10 mol% loading of catalyst under mild conditions.This atom economic reaction could be run on a gram scale without impacting its enantioselectivity.The absolute stereochemistry of catalytic products was determined by correlation with a known configuration compound.A possible mechanism was proposed for the asymmetric induction.