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Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters.

Zhiyang LiYichen LiXingguang LiMandi WuMing-Liang HeJianwei Sun
Published in: Chemical science (2021)
A new catalytic asymmetric formal cross dehydrogenative coupling process for the construction of all-aryl quaternary stereocenters is disclosed, which provides access to rarely explored chiral tetraarylmethanes with excellent enantioselectivity. The suitable oxidation conditions and the hydrogen-bond-based organocatalysis have enabled efficient intermolecular C-C bond formation in an overwhelmingly crowded environment under mild conditions. para-Quinone methides bearing an ortho-directing group serve as the key intermediate. The precise loading of DDQ is critical to the high enantioselectivity. The chiral products have also been demonstrated as promising antiviral agents.
Keyphrases
  • electron transfer
  • room temperature
  • capillary electrophoresis
  • ionic liquid
  • hydrogen peroxide
  • mass spectrometry
  • visible light
  • transition metal
  • nitric oxide