@article{6ee2f1af61ec467da606c40559f095a1,
title = "cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine",
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.",
author = "Kiyoto Hori and Hiroyasu Sugihara and Ito, {Yoshio N.} and Tsutomu Katsuki",
note = "Funding Information: As shown here, we were able to reveal the high potentiality of diaziridine as a nitrogen donor agent. The ready availability of diaziridine and simple one-pot operation makes the reaction useful as an efficient synthetic method of N-unsubstituted c/s-aziridine amides. Further investigations on the diaziridine chemistry are under way in our laboratory. Acknowledgment: Financial support from a Grant-in-Aid for Scientific Research from the l~nistry of Education, Science, Sports and Culture, Japan is gratefully acknowledged.",
year = "1999",
month = jul,
day = "9",
doi = "10.1016/S0040-4039(99)00939-9",
language = "English",
volume = "40",
pages = "5207--5210",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "28",
}