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Title

Allene-Based Gold-Catalyzed Stereodivergent Synthesis of Azapolycyclic Derivatives of Unusual Structure

AuthorsAlcaide, Benito ; Almendros, Pedro ; Martín-Montero, Raúl; Ruiz, M. Pilar
KeywordsSelectivity
Synthetic methods
Allenes
Gold
Heterocyclic compounds
Issue Date2016
PublisherJohn Wiley & Sons
CitationAdvanced Synthesis and Catalysis 358: 1469-1477 (2016)
AbstractThe present study provides insights into the manner in which the configuration of β-aminoallene precursors affects their gold-catalyzed cyclization reactions. The reactivity can be switched by using indolizidinone-tethered β-aminoallenes bearing the syn- or the anti-disposition of both protons at the α- and β-allenic stereocenters. Fused heterocycles (seven examples, 60-75% yields) are obtained from the syn-precursors, while a dimerization-aminoketalization-spirocyclization sequence to afford benzo[b]pyrrolo[3,2,1-ij][1,7]naphthyridin-1-ones (four examples, 34-48% yields) can be achieved starting from their anti-isomers.
Publisher version (URL)http://dx.doi.org/10.1002/adsc.201501145
URIhttp://hdl.handle.net/10261/133048
DOI10.1002/adsc.201501145
Identifiersdoi: 10.1002/adsc.201501145
issn: 1615-4150
e-issn: 1615-4169
Appears in Collections:(IQOG) Artículos
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