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Título: | Three-step metal-promoted allene-based preparation of Bis(heterocyclic) cyclophanes from carbonyl compounds |
Autor: | Alcaide, Benito CSIC ORCID; Almendros, Pedro CSIC ORCID ; Quirós, M. Teresa; Lázaro, Carlos; Torres, M. Rosario | Fecha de publicación: | 2014 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 79: 6244- 6255 (2014) | Resumen: | A 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. | URI: | http://hdl.handle.net/10261/102043 | DOI: | 10.1021/jo500993x | Identificadores: | doi: 10.1021/jo500993x issn: 0022-3263 e-issn: 1520-6904 |
Aparece en las colecciones: | (IQOG) Artículos |
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