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Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones

The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Na...

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Detalles Bibliográficos
Autores principales: Solas, Marta, Suárez‐Pantiga, Samuel, Sanz, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9544548/
https://www.ncbi.nlm.nih.gov/pubmed/35785510
http://dx.doi.org/10.1002/anie.202207406
Descripción
Sumario:The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions.