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Organocatalytic synthesis of 5-hydroxyisoxazolidine catalyzed by camphor sulfonyl hydrazines through aza-Michael addition/cyclization.

Fang-Fang XuLing-Yan ChenPeng SunYixin LvYan-Xue ZhangJia-Yu LiXiaoying YinYa Li
Published in: Chirality (2020)
A series of chiral 5-hydroxy isoxazolidines has been successfully synthesized through camphor sulfonyl hydrazine-catalyzed asymmetric aza-Michael addition reaction between N,O-protected hydroxyamines and enals. Moderate yields with moderate to good enantioselectivities (up to 96% enantiomeric excess [ee]) were achieved. It provides an alternative asymmetric approach to preparing isoxazolidine derivatives.
Keyphrases
  • room temperature
  • high intensity
  • capillary electrophoresis
  • solid state
  • ionic liquid
  • fluorescent probe
  • mass spectrometry
  • structure activity relationship