Synthesis of Benzofuranones via Malonates Desymmetrization: Yield Increase by the Portion-wise Addition of Quinones.

@article{Puglisi2018SynthesisOB,
  title={Synthesis of Benzofuranones via Malonates Desymmetrization: Yield Increase by the Portion-wise Addition of Quinones.},
  author={Antonio Puglisi and Chiara Giustini and Angela Ricucci and Elisa Perotti and Luca Massaro and Diego Morra and Flavia Ciucci and Alessio Zucchet and Achille Antenucci and Mauro Moliterno and Simone Placidi and Fabio Sciubba and Luciano Galantini and Riccardo Salvio and Marco Bella},
  journal={Chemistry},
  year={2018},
  volume={24 27},
  pages={
          6941-6945
        }
}
The organocatalyzed addition of several malonates to 1,4-benzoquinones affords benzofuranones bearing a quaternary stereocenter with good enantioselectivity. This reaction is an intramolecular desymmetrization since it proceeds through the formation of an arylated achiral malonate that cyclizes to give the reaction product. The addition rate of the quinone dramatically affects the reaction yield which was originally low. The yield was considerably increased, in some cases, from less than 20… CONTINUE READING
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