Asymmetric Oxidation Using Polymer-Supported Chiral Metalloporphyrins

Significance

Polystyrene-divinylbenzene (PS-DVB)-supported chiral metalloporphyrins 1 (M = Fe) and 2 (M = Ru) were prepared, and their catalytic activities were examined for asymmetric oxidation of sulfide and styrene derivatives. The PS-DVB-supported metalloporphyrins 1 and 2 were prepared by the polymerization of chiral metalloporphyrins having four vinyl groups with styrene and divinylbenzene. The asymmetric sulfoxidation of the alkyl aryl sulfides took place in the presence of iron porphyrin 1 to give the sulfoxides in 45-84% yields with 49-75% ee (eq. 1). The asymmetric epoxidation of the styrene derivatives proceeded in the presence of ruthenium porphyrin 2 to give the epoxides in 30-89% yields with 44-74% ee (eq. 2). Catalyst 1 was reused 15 times for the asymmetric oxidation of thioanisole.