Abstract

This review describes recent progress in the development of homogeneous, metal-mediated, catalytic pathways to synthetically valuable aziridines and sulfonamides. Areas of investigation described within this review include: (a) catalytic copper, iron, and silver-mediated nitrene transfer from the iminoiodinanes to olefins, (b) development of alternative nitrene sources for olefin aziridination, including N-halo-p-toluene sulfonamides, iminoiodinanes featuring labile N-protecting groups, and sulfonylazides, (c) use of single-pot aziridination protocols for the in situ generation of iminoiodinanes, and (d) metal-mediated carbene transfer to imines.

Keywords: catalytic transformations, ethyl diazoacetate (eda), cyclopropanation, aziridination, polydentate macrocyclic ligands, sulfur-containing macrocycles, esi-ms, recrystallization, metalloporphyrins, photolysis