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Cyclization of propargylic amides: mild access to oxazole derivatives

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The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxaz...

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Hauptverfasser: Weyrauch, Jan P. (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Schuster, Andreas M. (VerfasserIn) , Hengst, Tobias (VerfasserIn) , Schetter, Stefanie (VerfasserIn) , Littmann, Anna Christina (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Hamzić, Melissa (VerfasserIn) , Visus, Jorge (VerfasserIn) , Rominger, Frank (VerfasserIn) , Frey, Wolfgang (VerfasserIn) , Bats, Jan W. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: [January 18, 2010]
In: Chemistry - a European journal
Year: 2010, Jahrgang: 16, Heft: 3, Pages: 956-963
ISSN:1521-3765
DOI:10.1002/chem.200902472
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.200902472
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200902472
Volltext
Verfasserangaben:Jan P. Weyrauch, A. Stephen K. Hashmi, Andreas Schuster, Tobias Hengst, Stefanie Schetter, Anna Littmann, Matthias Rudolph, Melissa Hamzic, Jorge Visus, Frank Rominger, Wolfgang Frey, and Jan W. Bats
Beschreibung
Zusammenfassung:The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga’s reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.
Beschreibung:First published: 14 January 2010
Gesehen am 29.11.2023
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.200902472

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