cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine

Kiyoto Hori, Hiroyasu Sugihara, Yoshio N. Ito, Tsutomu Katsuki

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Aziridination of αβ-unsaturated amides was effected by treatment with lithiated 3,3-pentamethylenediaziridine in high diastereoselectivity, cis- Aziridine was the predominant diastereomer irrespective of the geometry of the substrates. A stepwise mechanism, 1,4-addition of a lithiated diaziridine to α,β-unsaturated amides and subsequent ring closure at the nitrogen atom, was proposed to explain the unusual cis-selectivity.

Original languageEnglish
Pages (from-to)5207-5210
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number28
DOIs
Publication statusPublished - Jul 9 1999

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Amides
Nitrogen
Atoms
Geometry
Substrates
aziridine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine. / Hori, Kiyoto; Sugihara, Hiroyasu; Ito, Yoshio N.; Katsuki, Tsutomu.

In: Tetrahedron Letters, Vol. 40, No. 28, 09.07.1999, p. 5207-5210.

Research output: Contribution to journalArticle

Hori, Kiyoto ; Sugihara, Hiroyasu ; Ito, Yoshio N. ; Katsuki, Tsutomu. / cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 28. pp. 5207-5210.
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