Iodine atom transfer [3 + 2] cycloaddition reaction with electron-rich alkenes using N-tosyliodoaziridine derivatives as novel azahomoallyl radical precursors

Osamu Kitagawa, Shinsaku Miyaji, Yoichiro Yamada, Hiroki Fujiwara, Takeo Taguchi

研究成果: Article

28 引用 (Scopus)

抜粋

Treatment of N-tosyliodoaziridine derivatives with Et3B efficiently produces various azahomoallyl radical (2-akenylamidyl radical) species which give oxygen-functionalized pyrrolidine derivatives through iodine atom transfer [3 + 2] cycloaddition with electron-rich alkenes such as enol ethers and ketene acetal. The present cycloaddition reaction proceeds regioselectively via C-N bond cleavage of an aziridinylalkyl radical intermediate and addition of the resulting azahomoallyl radicals to the terminal carbon of an alkene. The reaction of alkenes with the cyclohexenylamidyl radical generated from an optically active bicyclic iodoaziridine [(1S,2S,6S)-2-iodo-7-(p-toluenesulfonyl)-7-azabicyclo[4.1.0]heptane, 94% eel also proceeds to give optically active octahydroindole derivatives (84-93% ee).

元の言語English
ページ(範囲)3184-3189
ページ数6
ジャーナルJournal of Organic Chemistry
68
発行部数8
DOI
出版物ステータスPublished - 2003 4 18
外部発表Yes

ASJC Scopus subject areas

  • Organic Chemistry

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