4.8 Article

Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates

Journal

ORGANIC LETTERS
Volume 14, Issue 3, Pages 800-803

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol203331r

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Funding

  1. National Institutes of Health [GM 46503]
  2. National Science Foundation [CHE-0748121]
  3. Division Of Chemistry
  4. Direct For Mathematical & Physical Scien [0748121] Funding Source: National Science Foundation

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Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.

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