4.7 Article

Organocatalysed decarboxylative protonation process from Meldrum's acid: enantioselective synthesis of isoxazolidinones

Journal

CHEMICAL COMMUNICATIONS
Volume 49, Issue 98, Pages 11569-11571

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc47695b

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Funding

  1. INSA Rouen
  2. Rouen University
  3. CNRS
  4. EFRD
  5. Labex SynOrg [ANR-11-LABX-0029]
  6. European Union through a FEDER support engaged in region Haute-Normandie [34209, 33236]

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An asymmetric organocatalysed decarboxylative protonation reaction allowed a straightforward synthesis of alpha-substituted isoxazolidin-5-ones from readily available 5-substituted Meldrum's acids. This process is initiated by an anionic formal (3+2) cycloaddition-fragmentation, generated in-situ from a sulfone-amide precursor which also served as a latent source of proton.

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