[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.
Ohno
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Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
D000466:Alkadienes / Q000737:chemistry*; D001384:Azetidines / Q000138:chemical synthesis*; D001388:Aziridines / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic; D055601:Organic Chemistry Phenomena; D010165:Palladium
D000466:Alkadienes; D001384:Azetidines; D001388:Aziridines; D010165:Palladium