title: One-pot stereoselective synthesis of 2-acylaziridines and 2-acylpyrrolidines from N-(propargylic)hydroxylamines.
abstract: The stereoselective direct transformation of N-(propargylic)hydroxylamines into cis-2-acylaziridines was achieved by the combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4-isoxazolines into 2-acylaziridines and both 3-aryl- and 3-alkyl-substituted 2-acylaziridines could be prepared by using this method. Furthermore, subsequent 1,3-dipolar cycloaddition of azomethine ylides that were generated in situ from the intermediary 2-acylaziridines with maleimides was achieved in a stereoselective one-pot procedure to afford the corresponding 2-acylpyrrolidines, which consisted of an octahydropyrrolo[3,4-c]pyrrole skeleton.
authors: Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan.
authors: Yoshiaki
authors: Y
authors: Miyamoto
authors: Norihiro
authors: N
authors: Wada
authors: Takahiro
authors: T
authors: Soeta
authors: Shuhei
authors: S
authors: Fujinami
authors: Katsuhiko
authors: K
authors: Inomata
authors: Yutaka
authors: Y
authors: Ukaji
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006898:Hydroxylamines / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D001388:Aziridines; D001391:Azo Compounds; D006898:Hydroxylamines; D008301:Maleimides; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D003300:Copper; C029892:cupric chloride