Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

Hiroyuki Ishihara; Yoshio N. Ito; Tsutomu Katsuki

doi:10.1246/cl.2001.984

Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

Hiroyuki Ishihara, Yoshio N. Ito, Tsutomu Katsuki

有機・生物化学

研究成果: ジャーナルへの寄稿 › 記事

13 引用（Scopus）

抜粋

Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.

元の言語	英語
ページ（範囲）	984-985
ページ数	2
ジャーナル	Chemistry Letters
発行部数	10
DOI	https://doi.org/10.1246/cl.2001.984
出版物ステータス	出版済み - 1 1 2001

フィンガープリント

All Science Journal Classification (ASJC) codes

Chemistry(all)

これを引用

Ishihara, H., Ito, Y. N., & Katsuki, T. (2001). Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine. Chemistry Letters, (10), 984-985. https://doi.org/10.1246/cl.2001.984

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AB - Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.

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文献にアクセス

10.1246/cl.2001.984