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Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction.

Hui-Xuan ChenYaqi ZhangYuyang ZhangXuefeng HeZhen-Wei ZhangHao LiangWenhuan HeXiaoding JiangXiangmeng ChenLiqin Qiu
Published in: RSC advances (2018)
By means of the direct condensation of N -aminoethylpyrroles and isatins, followed by a chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction, a new class of valuable chiral 3',4'-dihydro-2' H -spiro[indoline-3,1'-pyrrolo[1,2- a ]pyrazin]-2-ones bearing a quaternary carbon stereocenter were successfully synthesized in good to excellent yields and with moderate to good enantioselectivities under mild reaction conditions.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • room temperature
  • mass spectrometry
  • high intensity