A Mild and Highly Chemoselective α-Iodination of N-Allylic Carboxamides and Lactams

Osamu Kitagawa, Norihiko Kikuchi, Tokushi Hanano, Katsuyuki Aoki, Tomomi Yamazaki, Midori Okada, Takeo Taguchi

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Abstract

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.

Original languageEnglish
Pages (from-to)7161-7165
Number of pages5
JournalJournal of Organic Chemistry
Volume60
Issue number22
DOIs
Publication statusPublished - 1995 Nov 1

ASJC Scopus subject areas

  • Organic Chemistry

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    Kitagawa, O., Kikuchi, N., Hanano, T., Aoki, K., Yamazaki, T., Okada, M., & Taguchi, T. (1995). A Mild and Highly Chemoselective α-Iodination of N-Allylic Carboxamides and Lactams. Journal of Organic Chemistry, 60(22), 7161-7165. https://doi.org/10.1021/jo00127a021