No abstract

The ring-enlargement of oxaziridines such as (I) to the lactams (II) is performed in the presence of a catalytic amount of a metalloporphyrin. Due to migration of the C-3 substituent cis to the lone pair of the ring nitrogen the reaction is stereoselective (. fwdarw. (IV), (V)) and gives the opposite selectivity compared with the corresponding photochemical and thermal rearrangements. -(SUDA, K.; SASHIMA, M.; IZUTSU, M.; HINO, F.; J. Chem. Soc., Chem. Commun. (1994) 8, 949-950; Meiji Coll. Pharm., Setagaya, Tokyo 154, Japan; EN)