Abstract

This paper describes the synthesis of both soluble and insoluble polymer-supported chiral (salen)Mn complexes and their use in asymmetric epoxidation reactions. These studies were undertaken to establish whether high enantioselectivities could be achieved with a polymer-bound catalyst and if the complexes could be recovered and reused for multiple cycles. Poly(ethylene glycol) monomethyl ether (MeO-PEG) and non-cross-linked polystyrene (NCPS) were used as soluble supports while JandaJel and Merrifield resins served as insoluble supports. Each polymer was linked to the salen catalyst through a glutarate spacer. The soluble catalysts were recovered by precipitation with a suitable solvent while the insoluble catalysts were simply filtered from the reaction mixture. Three olefins were utilized as epoxidation substrates: styrene, cis-β-methylstyrene, and dihydronaphthalene. Best results were obtained with cis-β-methylstyrene as the enantioselectivity obtained with each polymer-bound catalyst (86−90%) was equ...

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