Hydroxyl Functionalized Methacrylic Terpolymers as Supports for Mn(III) Salen Catalysts and Their Application in Asymmetric Epoxidation

Hydroxyl functionalized gel type resins derived from 2-hydroxyethyl, 2-hydroxypropyl and 2-hydroxy-3-phenoxypropyl methacrylates were applied to covalent immobilization of Mn(salen) complexes via glutarate and carbonate linkers. The obtained catalysts were characterized by FTIR and DR UV–Vis methods and elemental analysis. It was found that the activity of polymeric catalysts obtained in this way depended on both the nature of the functional and cross-linking monomers and the degree of the cross-linking of polymer matrices and the way of complex immobilization. The highest activity was observed for the complexes immobilized on the HEMA resins cross-linked with 3%-mol of diethylene glycol dimethacrylate. For instance, in the presence of the catalysts with (S,S)-salen ligand S-epoxystyrene and (1S, 2R)-epoxyindene could be obtained with 46% and 69% ee, respectively. Attempts have also been made to recycle the selected catalyst. However, a rapid fall off in the activity was observed, although the selectivity was similar in which three cycles.