4.6 Article

Enantioselective conjugate addition of 3-fluorooxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 32, Pages 5217-5221

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41267a

Keywords

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Funding

  1. National University of Singapore [R-143-000-469-112]
  2. GSK-EDB [R-143-000-491-592]
  3. Singapore-Peking-Oxford Research Enterprise [COY-15-EWI-RCFSA/N197-1]
  4. Ministry of Education (MOE) of Singapore [R-143-000-494-112]

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An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.

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