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Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones.

Chun-Bao MiaoAn-Qi ZhengLi-Jin ZhouXinyu LyuHai-Tao Yang
Published in: Organic letters (2020)
A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.
Keyphrases
  • amino acid
  • structure activity relationship
  • hydrogen peroxide
  • molecularly imprinted
  • high resolution
  • visible light
  • tandem mass spectrometry