Organic letters

1523-705217232015Dec04Organic lettersOrg LettIndium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-Reclosure.584658495846-910.1021/acs.orglett.5b03021A 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.SengokuTetsuyaTDepartment of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.MurataYusukeYGraduate School of Science and Technology, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.AsoYuwaYDepartment of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.KawakamiAiADepartment of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.InuzukaToshiyasuTDivision of Instrumental Analysis, Life Science Research Center, Gifu University , 1-1 Yanagido, Gifu 501-1193, Japan.SakamotoMasamiMDepartment of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University , 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.TakahashiMasakiMDepartment of Applied Chemistry, Faculty of Engineering, Shizuoka University , 3-5-1 Johoku, Naka-ku, Hamamatsu 432-8561, Japan.YodaHidemiHDepartment 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.engJournal ArticleResearch Support, Non-U.S. Gov't20151118