Synthesis, Characterization and Reactions of Enantiomerically Pure ‘Winged’ Spirane Porphyrazines

A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from l-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities (<25%).