The Kinetic Resolution Of α-Substituted Aminomethyl Ferrocene Via Palladium-Catalyzed C-H Functionalization

This thesis focuses on the kinetic resolution of α-substituted aminomethyl ferrocene via Palladium-catalyzed asymmetric dehydrogenative Heck reaction. The main results obtained are as follows:We realized the kinetic resolution of α-substituted aminomethyl ferrocene in the presence of Pd-catalysis with α-chiral amino acids as ligand to synthesize a series of 1, 2-disubstituted ferrocene derivatives with both center and planar chirality. It was found that the steric hindrance of the protecting group on nitrogen atom of chiral amino acids has a critical impact on the diastereo- and enantio-selectivities. This reaction has good applicability for different kinds of olefins such as acrylate, styrene, acrylamide and acrylic ketones. The moderate to good e.e. values 31-83% with high d.r.(93:7-98:2) and 8-76% yields for products and 4-96% e.e. values with the recovery of 14-83% of starting materials were obtained, The S values, the efficiency of resolution, are 4.6-12.7. The advantage of this kinetic resolution reaction can be gained through regulating the reaction progress to get either products or starting materials in high optical activity.