Oxaziridine rearrangements in asymmetric synthesis

Oxaziridines undergo photochemical rearrangement reactions to afford chiral lactams with high levels of enantio- or regio-selectivity, This reaction was applied to the synthesis of targets such as carnitine, the yohimbine alkaloids, and several classes of peptidomimetics, In addition, single-electron transfer reactions can be elicited from oxaziridines using Cu-I. These reactions afford nitrogen and carbon radicals that add to an appended olefin, with the final products depending on both the substitution and stereochemistry of the starting oxaziridine.