Mild and highly chemoselective a-iodination reactions of N-allylic carboxamides and lactams are reported. N-Allylic amides and lactams reacted with I2 and 2,6-lutidine at room temperature to give α-iodo amides and lactams in moderate to good yields. The exclusive α-iodination of N-allylic amides having another acidic hydrogen in the molecule proceeded under these conditions. The iodides obtained were converted to the bicyclic lactam or the β-lactam derivatives with high stereoselectivity by a radical iodine atom-transfer reaction or a nucleophilic substitution reaction.
|Number of pages||5|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1995 Nov 1|
ASJC Scopus subject areas
- Organic Chemistry