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

AuthorsAlcaide, Benito ; Almendros, Pedro ; Quirós, M. Teresa; Lázaro, Carlos; Torres, M. Rosario
Issue Date2014
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 79: 6244- 6255 (2014)
AbstractA 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.
Identifiersdoi: 10.1021/jo500993x
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IQOG) Artículos
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