4.8 Article

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

Journal

ORGANIC LETTERS
Volume 20, Issue 3, Pages 684-687

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03818

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Funding

  1. Yale University
  2. Sloan Foundation
  3. National Science Foundation (CAREER) [1653793]
  4. National Institutes of Health [T32GM067543]
  5. Division Of Chemistry
  6. Direct For Mathematical & Physical Scien [1653793] Funding Source: National Science Foundation

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The use of allyl-palladium catalysis for the one-step alpha,beta-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)(2) as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

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