4.8 Article

Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones

Journal

ORGANIC LETTERS
Volume 13, Issue 22, Pages 6122-6125

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2026125

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Funding

  1. National Institutes of Health [GM 46503]
  2. National Science Foundation [CHE-0748121]

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The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).

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