铟催化的 N-羰基亚胺的酰胺烯丙基化反应：通过开环-闭环反应形成氮杂螺-γ-内酰胺。
Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-Reclosure.
机构信息
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.
出版信息
Org Lett. 2015 Dec 4;17(23):5846-9. doi: 10.1021/acs.orglett.5b03021. Epub 2015 Nov 18.
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.
本文描述了一种从 N-羰基酰亚胺出发，合成具有亚甲基-内酰胺骨架的氮杂螺-γ-内酰胺的新颖、简便方法。机理研究提供了证据，表明该反应经历了两步反应过程，首先是 ZnCl(2)促进的β-酰胺烯丙基铟物种加成，然后是出乎意料的分子筛介导的开环-闭环同时失去一个 N-羰基单元。
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