4.8 Article

Asymmetric synthesis of chiral cycloalkenone derivatives via palladium catalysis

Journal

CHEMICAL SCIENCE
Volume 5, Issue 4, Pages 1354-1360

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc53250j

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Funding

  1. National Institutes of Health [GM33049]
  2. National Science Foundation [CHE-0948222]
  3. Abbott Laboratories Stanford Graduate Fellowship
  4. NIH [GM083428]
  5. Direct For Mathematical & Physical Scien
  6. Division Of Chemistry [1145236] Funding Source: National Science Foundation

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The palladium-catalyzed oxidative desymmetrization of meso-dibenzoates yields g-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

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