Oxiziridine rearrangements in asymmetric synthesis

Abstract

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 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.

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