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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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Bibliographic Details
Main Authors: Zhao, Ximei (Author) , Tian, Bing (Author) , Yang, Yangyang (Author) , Si, Xiaojia (Author) , Mulks, Florian (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 29 March 2019
In: Advanced synthesis & catalysis
Year: 2019, Volume: 361, Issue: 13, Pages: 3155-3162
ISSN:1615-4169
DOI:10.1002/adsc.201900264
Online Access: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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Author Notes:Ximei Zhao, Bing Tian, Yangyang Yang, Xiaojia Si, Florian F. Mulks, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Version of record online: April 29, 2019
Gesehen am 12.11.2019
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201900264

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