Through catalytic epoxidation and aziridination of olefins versatile synthetic intermediates and subunits of biologically active compounds and pharmaceuticals –epoxides and aziridines– can be obtained. The focus of this review is on recent advances in the epoxidation and aziridination of challenging terminal alkenes with respect to safety of solvents or reagents used and atom economy aspects, as well as scope and limitations of developed non-heme iron catalysts. The still large research potential for sustainable and environmentally attractive iron-based catalysts in enantioselective epoxide and aziridine synthesis is demonstrated.