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Synthesis of 1,2,3-trisubstituted and 1,2,2,3-tetrasubstituted aziridines from α-chloroketimines

Norbert De Kimpe*, Luc Moens

*Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium, Email:

N. De Kimpe, L. Moens, Tetrahedron, 1990, 46, 2965-2974.

DOI: 10.1016/S0040-4020(01)88388-5


Secondary α-chloroketimines react with lithium aluminium hydride in ether to afford mixtures of cis- and trans-1,2,3-trisubstituted aziridines by nucleophilic addition of hydride across the imino bond and subsequent intramolecular nucleophilic substitution. Tertiary α-chloroketimines react similarly to yield 1,2,2,3-tetrasubstituted aziridines. α,α-Dichloroketimines react in a stereospecific way to afford cis-aziridines, exclusively.

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Key Words

De Kimpe Aziridine Synthesis, Lithium aluminium hydride

ID: JXX-Y1990-0800