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

Hiroyuki Ishihara, Yoshio N. Ito, Tsutomu Katsuki

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13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)984-985
Number of pages2
JournalChemistry Letters
Issue number10
DOIs
Publication statusPublished - Jan 1 2001

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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