A chiral Mn-III-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 O-2 as terminal oxidant in the presence of isobutyraldehyde. The catalyst showed higher enantioselectivity than its homogeneous counterpart in the oxidation of alpha-methylstyrene. SBA15-[Mn(TCPP-R*)Cl] catalyzed epoxidation of styrene was achieved within 8 h and optically active styrene oxide was obtained in 89% ee and 90% yield. Likewise, styrene derivatives (trans-beta-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. (C) 2017 Elsevier Inc. All rights reserved.