[Development of aziridination and azetizination reactions of amino allenes using a palladium catalyst].

Palladium-catalyzed synthesis of alkenylaziridines and azetidines from alpha- and beta-amino allenes are presented. Whereas palladium-catalyzed reaction of N-arylsulfonyl-alpha-amino allenes with an aryl iodide in the presence of potassium carbonate in DMF at around 70 degrees C affords the corresponding 3-pyrroline derivatives, the reaction in refluxing 1,4-dioxane under similar conditions yields exclusively or most predominantly the corresponding 2-alkenylaziridines bearing an aryl group on the double bond. Similarly, N-arylsulfonyl-beta-amino allenes can be also cyclized into the corresponding alkenylazetidines bearing 2,4-cis-sunstituents under palladium-catalyzed cyclization conditions in DMF.