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Catalytic asymmetric de novo construction of dihydroquinazolinone scaffolds via enantioselective decarboxylative [4+2] cycloadditions.

Yi-Nan LuJin-Ping LanYu-Jia MaoYe-Xin WangGuang-Jian MeiFeng Shi
Published in: Chemical communications (Cambridge, England) (2018)
The first de novo construction of enantioenriched dihydroquinazolinones via an intermolecular strategy has been established. This approach also represents the first catalytic asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with sulfonyl isocyanates, which afforded chiral dihydroquinazolinones in high yields and excellent enantioselectivities (up to 98% yield, 99 : 1 er). This reaction not only confronts the great challenge in de novo construction of enantioenriched dihydroquinazolinone skeletons, but also advances the chemistry of decarboxylative cycloadditions involving vinyl benzoxazinanones.
Keyphrases
  • visible light
  • crystal structure
  • solid state
  • estrogen receptor
  • ionic liquid
  • tissue engineering
  • endoplasmic reticulum
  • mass spectrometry
  • drug discovery