Gold-catalyzed stereoselective domino cyclization/alkynylation of N-propargylcarboxamides with benziodoxole reagents for the synthesis of alkynyloxazolines
A concise and highly stereoselective synthesis of alkynyloxazolines via a gold-catalyzed domino cyclization-alkynylation cascade of N-propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternative to two step sequences based on Sonagashira...
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| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
29 March 2019
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| In: |
Advanced synthesis & catalysis
Year: 2019, Jahrgang: 361, Heft: 13, Pages: 3155-3162 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201900264 |
| Online-Zugang: | Resolving-System, Volltext: https://doi.org/10.1002/adsc.201900264 Verlag: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201900264 
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| Verfasserangaben: | Ximei Zhao, Bing Tian, Yangyang Yang, Xiaojia Si, Florian F. Mulks, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Zusammenfassung: | A concise and highly stereoselective synthesis of alkynyloxazolines via a gold-catalyzed domino cyclization-alkynylation cascade of N-propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternative to two step sequences based on Sonagashira couplings, offers a broad substrate scope, excellent functional group tolerance, and perfect stereoselectivity. A comparison of the computed energies of the isomers of the product suggests kinetic control as the cause of the observed selectivity. |
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| Beschreibung: | Version of record online: April 29, 2019 Gesehen am 12.11.2019 |
| Beschreibung: | Online Resource |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201900264 |