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

研究成果: Article査読

18 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)7161-7165
ページ数5
ジャーナルJournal of Organic Chemistry
60
22
DOI
出版ステータスPublished - 1995 11 1
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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