Highly diastereoselective epoxidation of cholest-5-ene derivatives catalyzed by polymer-supported manganese(III) porphyrins

Abstract

Abstract Manganese(III) 5,10,15-tris(tolyl)-20-(4-hydroxyphenyl) porphyrin covalently attached to Merrifield’s peptide resin (MPR) was prepared. The catalysts exhibit high reactivity and β-selectivity toward the epoxidation of cholest-5-ene derivatives with PhIO. Under mild reaction conditions, the catalyst was consecutively reused four times without detectable catalyst leaching and gave over 90% epoxide yield and over 99% β-selectivity.