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N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated γ-Lactams and Their N-α-Methoxylated Derivatives: Application to an Expeditive Synthesis of (±)-Crispine A
Synthesis ( IF 2.2 ) Pub Date : 2020-06-23 , DOI: 10.1055/s-0040-1707886
Joëlle Pérard-Viret 1 , Florence Souquet 1 , Wassila Drici 2 , Sandra Abi Fayssal 1 , Imane Lazouni 2 , Sébastien Thueillon 1
Affiliation  


Dedicated to Dr. Jacques Royer

Abstract

An improved synthesis of unsaturated γ-lactams by condensation of various primary amines with 2,5-dimethoxy-2,5-dihydrofuran is described. A modified mechanism for this reaction is suggested. Synthesis of their N-α-methoxylated derivatives, as N-acyliminium ion precursors, is also reported. Finally, a short synthesis of (±)-crispine A is presented as an illustrative application.



中文翻译:

N-酰基亚胺离子化学:改善获得不饱和γ-内酰胺及其N-α-甲氧基化衍生物的途径:在(±)-Crispine A的快速合成中的应用


献给雅克·罗耶(Jacques Royer)博士

抽象

描述了通过各种伯胺与2,5-二甲氧基-2,5-二氢呋喃缩合的改进的不饱和γ-内酰胺的合成。建议对该反应进行改进的机理。还报道了它们的N -α-甲氧基化衍生物,作为N-酰基亚胺离子前体的合成。最后,提出了(±)-crispine A的简短合成作为说明性应用。

更新日期:2020-06-24
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