Stereoselective Synthesis of 2-Alkenylaziridines and 2-Alkenylazetidines by Palladium-Catalyzed Intramolecular Amination of α- and β-Amino Allenes
The Journal of Organic Chemistry2001Vol. 66(14), pp. 4904–4914
Citations Over TimeTop 10% of 2001 papers
Hiroaki Ohno, Miyuki Anzai, Ayako Toda, Shinya Ohishi, Nobutaka Fujii, Tetsuaki Tanaka, Yoshiji Takemoto, Toshiro Ibuka
Abstract
Whereas palladium-catalyzed reaction of N-arylsulfonyl-alpha-amino allenes with an aryl iodide (4 equiv) in the presence of potassium carbonate (4 equiv) in DMF at around 70 degrees C affords the corresponding 3-pyrroline derivatives, the reaction in refluxing 1,4-dioxane under otherwise identical 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 a 2,4-cis-configuration under palladium-catalyzed cyclization conditions in DMF.
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