Diazomethane‐mediated C‐C bond cleavage of α‐keto N,O‐hemiaminals was investigated for the first time. Diazomethane as a reagent result C‐C bond cleavage of norbornyl α‐keto N,O‐hemiaminals, Grob‐like fragmentation, lead to the formation of cyclopentane annulated δ‐lactams in excellent yields. We have synthesized the precursor norbornyl α‐keto N,O‐hemiaminal by the nucleophilic displacement of halogen of norbornyl α‐diketone with the various amines.

中文翻译：

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通过重氮甲烷介导的α-酮N,O-半缩醛的C-C键断裂合成环戊烷环状δ-内酰胺


首次研究了重氮甲烷介导的 α-酮 N,O-半缩醛胺的 C-C 键断裂。重氮甲烷作为试剂导致降冰片基 α-酮 N,O-半缩醛胺的 C-C 键断裂，Grob 样断裂，从而以优异的产率形成环戊烷环状 δ-内酰胺。我们通过降冰片基 α-二酮的卤素与各种胺的亲核置换，合成了前体降冰片基 α-酮 N,O-半缩醛胺。