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

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Mild and highly chemoselective α-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
JournalThe Journal of Organic Chemistry
Volume60
Issue number22
Publication statusPublished - 1995
Externally publishedYes

Fingerprint

Lactams
Amides
Stereoselectivity
Iodides
Iodine
Hydrogen
Substitution reactions
Derivatives
Atoms
Molecules

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. The Journal of Organic Chemistry, 60(22), 7161-7165.

A mild and highly chemoselective α-iodination of N-allylic carboxamides and lactams. / Kitagawa, Osamu; Kikuchi, Norihiko; Hanano, Tokushi; Aoki, Katsuyuki; Yamazaki, Tomomi; Okada, Midori; Taguchi, Takeo.

In: The Journal of Organic Chemistry, Vol. 60, No. 22, 1995, p. 7161-7165.

Research output: Contribution to journalArticle

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', The Journal of Organic Chemistry, vol. 60, no. 22, pp. 7161-7165.
Kitagawa O, Kikuchi N, Hanano T, Aoki K, Yamazaki T, Okada M et al. A mild and highly chemoselective α-iodination of N-allylic carboxamides and lactams. The Journal of Organic Chemistry. 1995;60(22):7161-7165.
Kitagawa, Osamu ; Kikuchi, Norihiko ; Hanano, Tokushi ; Aoki, Katsuyuki ; Yamazaki, Tomomi ; Okada, Midori ; Taguchi, Takeo. / A mild and highly chemoselective α-iodination of N-allylic carboxamides and lactams. In: The Journal of Organic Chemistry. 1995 ; Vol. 60, No. 22. pp. 7161-7165.
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