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• W2072795390 abstract "Abstract In this paper we describe a new environmentally friendly method to promote the stereoselective epoxidation of Δ 4 ‐ and Δ 5 ‐steroids. Metalloporphyrins efficiently catalyze the epoxidation reactions of 17β‐acetoxy‐4‐androstene ( 1 ), 4‐cholestene ( 2 ) and 3β‐acetoxy‐5‐cholestene ( 3 ) in the presence of H 2 O 2 as oxygen donor. Modeling the molecular structure of the porphyrin as well as the central metal allows the control of the preferential formation of α‐ or β‐epoxides. Porphyrins with bulky, electron‐withdrawing groups in the ortho positions of the meso phenyls and with Mn III as the central metal ion, such as [Mn(TDCPP)Cl], gave preferentially the β‐epoxide of Δ 4 ‐ and Δ 5 ‐steroids. [Fe(TPFPP)Cl] catalyzes preferentially the α‐epoxidation of Δ 4 ‐steroids and also increases the stereoselectivity for the α‐epoxide in Δ 5 ‐steroids, similar to the results obtained with m ‐CPBA ( m ‐chloroperbenzoic acid) as oxidant. The substrate structure strongly influences the chemoselectivity of the reactions. The X‐ray structures of two main products were determined, and two‐dimensional NMR techniques allowed the full assignment of 1 H and 13 C NMR resonances as well as the stereochemistry of these products. A mechanistic proposal involving oxo species for the β‐approach and peroxy species for the α‐approach is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)" @default.
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• W2072795390 date "2004-11-15" @default.
• W2072795390 modified "2023-10-17" @default.
• W2072795390 title "Oxidation of Δ⁴‐ and Δ⁵‐Steroids with Hydrogen Peroxide Catalyzed by Porphyrin Complexes of Mn^III and Fe^III" @default.
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• W2072795390 doi "https://doi.org/10.1002/ejoc.200400461" @default.
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