A MILD AND HIGHLY CHEMOSELECTIVE ALPHA-IODINATION OF N-ALLYLIC CARBOXAMIDES AND LACTAMS

Mild and highly chemoselective alpha-iodination reactions of N-allylic carboxamides and lactams are reported. N-Allylic amides and lactams r eacted with I-2 and 2,6-lutidine at room temperature to give alpha-iod o amides and lactams in moderate to good yields. The exclusive alpha-i odination of N-allylic amides having another acidic hydrogen in the mo lecule proceeded under these conditions. The iodides obtained were con verted to the bicyclic lactam or the beta-lactam derivatives with high stereoselectivity by a radical iodine atom-transfer reaction or a nuc leophilic substitution reaction.