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Enantioselective [3 + 3] Annulation-Deoxalation Strategy for Rapid Access to δ-Oxoesters via N-Heterocyclic Carbene Catalysis.
Baranska, Izabela; Dobrzanska, Liliana; Rafinski, Zbigniew.
Afiliación
  • Baranska I; Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland.
  • Dobrzanska L; Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland.
  • Rafinski Z; Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland.
Org Lett ; 26(6): 1207-1211, 2024 Feb 16.
Article en En | MEDLINE | ID: mdl-38325001
ABSTRACT
A new and unprecedented stereoselective synthetic approach to δ-oxoesters derivatives from readily available starting materials has been developed. This method, catalyzed by N-heterocyclic carbene, involves an annulation-deoxalation reaction of alkynyl aldehydes with 2,4-diketoesters and proceeds via the chiral α,ß-unsaturated acylazolium intermediates. The annulation includes the in situ formation of dihydropyranones, which undergo ring-opening methanolysis with Lewis acid activation, followed by deoxalation to afford chiral 1,5-ketoesters in moderate to good yields.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Estados Unidos