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
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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 -