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 language | English |
|---|---|
| Pages (from-to) | 5207-5210 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 40 |
| Issue number | 28 |
| DOIs | |
| Publication status | Published - Jul 9 1999 |
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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 journal › Article
}
TY - JOUR
T1 - cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine
AU - Hori, Kiyoto
AU - Sugihara, Hiroyasu
AU - Ito, Yoshio N.
AU - Katsuki, Tsutomu
PY - 1999/7/9
Y1 - 1999/7/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0033538603&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033538603&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(99)00939-9
DO - 10.1016/S0040-4039(99)00939-9
M3 - Article
AN - SCOPUS:0033538603
VL - 40
SP - 5207
EP - 5210
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 28
ER -