Aziridination and amidation catalyzed by polymer-supported metalloporphyrins with PhI(OAc)2 and TsNH2

Manganese and ruthenium 5, 10, 15-tris(tolyl)-20-(4-hydroxyphenyl) porphyrins covalently attached to Merrifield's peptide resin( MPR) were prepared respectively. The catalysts efficiently catalyzed the aziridination/amidation of simple hydrocarbons and Delta(5)-steroid derivatives with PhI(OAc)(2) and TsNH2. Moderate to excellent yields were obtained under mild reaction conditions. The catalysts 3a and 3b exhibit different diasteroselectivities towards the Delta(5)-steroid derivatives, the former shows alpha-selectivity. and the later shows beta-selectivity under certain reaction conditions.