Abstract
A chiral MnIII-porphyrin complex covalently bonded with mesoporous SBA-15 (SBA15-[Mn(TCPP-R∗)Cl]) was synthesized and fully characterized. The heterogeneous SBA15-[Mn(TCPP-R∗)Cl] exhibited remarkable catalytic activity toward enantioselective olefin epoxidation using O2 as terminal oxidant in the presence of isobutyraldehyde. The catalyst showed higher enantioselectivity than its homogeneous counterpart in the oxidation of α-methylstyrene. SBA15-[Mn(TCPP-R∗)Cl] catalyzed epoxidation of styrene was achieved within 8h and optically active styrene oxide was obtained in 89% ee and 90% yield. Likewise, styrene derivatives (trans-β-methylstyrene, indene), conjugated cis- and trans-disubstituted olefins (e.g. cis- and tans-stilbene) and terminal olefins were converted effectively to their corresponding epoxides in 63–99%ee under the Mn(III)-catalyzed conditions. The catalyst could be recycled five times without any significant loss in activity.
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