Polar [3 + 2] cycloaddition of ketones with electrophilically activated carbonyl ylides. Synthesis of spirocyclic dioxolane indolinones.

@article{BentabedAbabsa2008Polar,
  title={Polar [3 + 2] cycloaddition of ketones with electrophilically activated carbonyl ylides. Synthesis of spirocyclic dioxolane indolinones.},
  author={Ghenia Bentabed-Ababsa and Aicha Derdour and Thierry Roisnel and Jos{\'e} Antonio S{\'a}ez and Luis Ramon Domingo and Florence Mongin},
  journal={Organic \& biomolecular chemistry},
  year={2008},
  volume={6 17},
  pages={
          3144-57
        }
}
The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and ketones (ethyl pyruvate, ethyl phenylglyoxylate, isatin, N-methylisatin and 5-chloroisatin) to give substituted dioxolanes and spirocyclic dioxolane indolinones was investigated. The effect of microwave irradiation on the outcome of the reaction was studied. The thermal reaction between 2,2-dicyano-3-phenyloxirane and N-methylisatin was theoretically studied using DFT methods. This reaction is a domino… 
27 Citations
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