English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/102043
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Three-step metal-promoted allene-based preparation of Bis(heterocyclic) cyclophanes from carbonyl compounds

AutorAlcaide, Benito ; Almendros, Pedro ; Quirós, M. Teresa; Lázaro, Carlos; Torres, M. Rosario
Fecha de publicación2014
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 79: 6244- 6255 (2014)
ResumenA straightforward metal-mediated method for the synthesis of bis(dihydrofuryl) cyclophane scaffolds from carbonyl compounds has been developed. The combination of the dihydrofuran moiety with different heterocycles such as β-lactams and sugars allows high levels of skeletal diversity. The process comprises indium-promoted one-pot carbonyl bis(allenylation) and gold- or palladium-catalyzed double cyclization in the resulting bis(allenols), followed by selective ruthenium-catalyzed macrocyclization. In some cases, the method has been successfully applied to the synthesis of the challenging Z-isomers. The E- versus Z-stereochemistry of the metathesis-formed double bonds could not be assigned taking into consideration the usual coupling constants criteria, but a diagnostic based on the chemical shifts of the two olefinic protons located at the macrocyclic double bond was established.
Identificadoresdoi: 10.1021/jo500993x
issn: 0022-3263
e-issn: 1520-6904
Aparece en las colecciones: (IQOG) Artículos
Ficheros en este ítem:
No hay ficheros asociados a este ítem.
Mostrar el registro completo

Artículos relacionados:

NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.