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

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

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,...

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Veröffentlicht in:Organic letters 2011-11, Vol.13 (22), p.6122-6125
Hauptverfasser: Xu, Xinfang, Ratnikov, Maxim O, Zavalij, Peter Y, Doyle, Michael P
Format: Artikel
Sprache:eng
Schlagworte:
Butyric Acid - chemistry
Catalysis
Copper - chemistry
Hydroxylation
Models, Molecular
Molecular Structure
Nitrogen Oxides - chemistry
Pyrroles - chemical synthesis
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Zusammenfassung: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2026125