Synthesis, configuration, and (15)n NMR spectra of iminoaziridines. Synthons equivalent to three components of the Ugi reaction.

Monocyclic iminoaziridines and exo-endo diastereomers of spirocyclic iminoaziridines that are derived from norbornane are prepared in batches of up to 10 g to foster applications as building blocks in syntheses. N,N'-Disubstituted alpha-haloamidines, which are readily available in two steps from N-substituted alpha-halocarboxamides, are 1,3-dehydrohalogenated by strong bases such as alkali-metal hydrides or tert-butoxides to afford distillable oils or low-melting solids, which consist of slowly interconverting E-Z diastereomers of the title compounds. The scope and limitations are outlined for this reaction.