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Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones.

Yun-Jie TsouRen-You GuanJeng-Liang Han
Published in: Organic & biomolecular chemistry (2022)
Spirocyclic o-quinone analogues show a broad spectrum of applications as biologically active compounds. We herein report the chiral bifunctional squaramide catalysed asymmetric vinylogous aldol-cyclization cascade reaction between 3-alkylidene oxindoles and o-quinones. A wide range of enantioenriched spirocyclic o-quinone analogues with a quaternary stereocenter could be smoothly synthesized in good to excellent yields (up to 99%) with high enantioselectivities (up to 99%).
Keyphrases
  • molecular docking
  • structure activity relationship
  • electron transfer
  • highly efficient
  • ionic liquid
  • molecular dynamics simulations
  • metal organic framework
  • solid state