Divergent synthesis of α-functionalized amides through selective N–O/C–C or N–O/C–C/C–N cleavage of aza-cyclobutanone oxime esters,Chemical Communications

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Divergent synthesis of α-functionalized amides through selective N–O/C–C or N–O/C–C/C–N cleavage of aza-cyclobutanone oxime esters
Chemical Communications ( IF 4.3 ) Pub Date : 2021-08-25 , DOI: 10.1039/d1cc03348d
Hua-Wei Liu ₁ , Dian-Liang Wang ₁ , Nan-Quan Jiang ₁ , Hai-Yan Li ₂ , Zhong-Jian Cai ₁ , Shun-Jun Ji ₁

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Herein, a novel sequential ring opening reaction of aza-cyclobutanone oxime esters with isocyanides is described. The reaction proceeded smoothly under redox-neutral and mild conditions, leading to a divergent synthesis of α-cyanomethylaminoamides, α-acyloxyamides and α-acylaminoamides. In these transformations, a selective N–O/C–C or N–O/C–C/C–N cleavage was achieved only by changing the iron-catalyst system. Among them, a rare sequential N–O/C–C/C–N cleavage process with a classical Passerini or Ugi multicomponent reaction can be executed in a single step. To the best of our knowledge, this work creates a novel reaction mode of cycloketone oximes and provides new opportunities for reaction design.

中文翻译：

通过氮杂环丁酮肟酯的选择性N-O/C-C或N-O/C-C/C-N裂解合成α-官能化酰胺

在此，描述了氮杂-环丁酮肟酯与异氰化物的新型顺序开环反应。该反应在氧化还原中性和温和条件下顺利进行，导致α-氰基甲基氨基酰胺、α-酰氧基酰胺和α-酰氨基酰胺的不同合成。在这些转化中，只有通过改变铁催化剂体系才能实现选择性 N-O/C-C 或 N-O/C-C/C-N 裂解。其中，可以在单个步骤中执行具有经典 Passerini 或 Ugi 多组分反应的罕见顺序 N-O/C-C/C-N 裂解过程。据我们所知，这项工作创造了一种新的环酮肟反应模式，并为反应设计提供了新的机会。

更新日期：2021-09-01

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