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

被引:0
|
作者
Ishihara, H [1 ]
Ito, YN [1 ]
Katsuki, T [1 ]
机构
[1] Kyushu Univ, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan
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中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with alpha,beta -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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页码:984 / 985
页数:2
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