4.8 Article

Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 10, Pages 3258-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja100041e

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Funding

  1. NSF [CHE-0969157]
  2. NIGMS [R01 GM084254]
  3. UCSB
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [0969157] Funding Source: National Science Foundation

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An expedient and reliable method for accessing reactive alpha-oxo gold carbenes via gold-catalyzed intermolecular oxidation of terminal alkynes has been developed. Significantly, this method offers a safe and economical alternative to the strategies based on diazo substrates. Its synthetic potential is demonstrated by expedient preparation of dihydrofuran-3-ones containing a broad range of functional groups.

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