抄録
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).
本文言語 | English |
---|---|
ページ(範囲) | 3184-3189 |
ページ数 | 6 |
ジャーナル | Journal of Organic Chemistry |
巻 | 68 |
号 | 8 |
DOI | |
出版ステータス | Published - 2003 4月 18 |
外部発表 | はい |
ASJC Scopus subject areas
- 有機化学