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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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Main Authors: Weyrauch, Jan P. (Author) , Hashmi, A. Stephen K. (Author) , Schuster, Andreas M. (Author) , Hengst, Tobias (Author) , Schetter, Stefanie (Author) , Littmann, Anna Christina (Author) , Rudolph, Matthias (Author) , Hamzić, Melissa (Author) , Visus, Jorge (Author) , Rominger, Frank (Author) , Frey, Wolfgang (Author) , Bats, Jan W. (Author)
Format: Article (Journal)
Language:English
Published: [January 18, 2010]
In: Chemistry - a European journal
Year: 2010, Volume: 16, Issue: 3, Pages: 956-963
ISSN:1521-3765
DOI:10.1002/chem.200902472
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.200902472
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200902472
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Author Notes: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
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Summary: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.
Item Description:First published: 14 January 2010
Gesehen am 29.11.2023
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.200902472

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