title: Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-Reclosure.
abstract: A novel and facile synthesis of azaspiro-γ-lactones with a methylene-lactam framework from N-carbonyl imides is described. Mechanistic investigations provide evidence for a two-step reaction process involving ZnCl(2)-promoted addition of β-amido allylindium species followed by an unexpectedly molecular-sieves-mediated ring opening-reclosure concomitantly with the loss of an N-carbonyl unit.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Sengoku
authors.affiliation: Graduate School of Science and Technology, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Murata
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Yuwa
authors.initials: Y
authors.lastname: Aso
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Ai
authors.initials: A
authors.lastname: Kawakami
authors.affiliation: Division of Instrumental Analysis, Life Science Research Center, Gifu University , 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Toshiyasu
authors.initials: T
authors.lastname: Inuzuka
authors.affiliation: Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University , 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Masami
authors.initials: M
authors.lastname: Sakamoto
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Masaki
authors.initials: M
authors.lastname: Takahashi
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.|Graduate School of Science and Technology, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.
authors.forename: Hidemi
authors.initials: H
authors.lastname: Yoda
mesh_terms: D000577:Amides / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D000577:Amides; D001372:Aza Compounds; D002712:Chlorides; D007094:Imides; D007769:Lactams; D007783:Lactones; D013141:Spiro Compounds; D017967:Zinc Compounds; D007204:Indium; C020758:indium trichloride; C016837:zinc chloride