Synthesis of Chiral Bitetralin-strapped “Twin Coronet” Porphyrins. Catalytic and Asymmetric Epoxidation of Styrene Derivatives

Abstract

Abstract “Twin-coronet” porphyrins bearing optically active 1,1′-bitetrahydronaphthalene derivatives on the both faces of the porphyrin were prepared as enantioselective oxidation catalysts modeling on cytochrome P-450s. The eclipsed isomer of the corresponding iron(III) porphyrins catalyzed epoxidation of styrenes substituted with electron-withdrawing groups in high e.e. (61–89%) and high product selectivity.