Summary: Novel polymers with chiral 1,2-diamine moiety were successfully synthesized by polycondensation of N-Boc protected enantiopure 1,2-diamine bearing two phenol groups (S,S)-4, bisphenol derivatives, and dibromides, followed by deprotection of N-Boc moiety. Hydrogenation of acetophenone was performed with use of polymeric catalyst system prepared from the polymer-supported chiral 1,2-diamine and RuCl₂/(S)-BINAP. The reaction proceeded smoothly even in 2-propanol to give 1-phenylethanol in quantitative yield with high level of enantioselectivity. Furthermore, various other aromatic ketones could be asymmetrically hydrogenated by the polymeric catalyst system.

Novel polymer-supported chiral 1,2-diamines have successfully synthesized by radical copolymerization of N-Boc protected enantiopure 1,2-diamine bearing two vinylphenyl moieties ((S,S)-5) with various achiral vinyl monomer including methyl methacrylate, 2-hydroxyethyl methacrylate, butyl acrylate, and N-isopropyl acrylamide, followed by deprotection of N-Boc moiety. Hydrogenation of acetophenone in 2-propanol/DMF mixed solvent was performed with use of polymeric catalyst system prepared from the polymer-supported chiral 1,2-diamine and RuCl₂/(S)-BINAP. The reaction proceeded smoothly to give 1-phenylethanol in quantitative yield with high level of enantioselectivity. In addition, various other aromatic ketones could be asymmetrically hydrogenated by the polymeric catalyst system. Furthermore, the polymeric catalyst could be reused several times in hydrogenation of aromatic ketones without loss of the enantioselectivity.