Oxiziridine 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 oxiziridine using CuI. 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.