A gold-catalyzed acid-assisted regioselective cyclization for the synthesis of polysubstituted oxazoles

Polysubstituted oxazole derivatives are obtained through a regioselective gold-catalyzed reaction of α-alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by alkyne oxidation with a pyridine N-oxide. Acidic conditions ensure that only one o...

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Main Authors: Wang, Qian (Author) , Hoffmann, Stephanie (Author) , Schießl, Jasmin (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 5 February 2020
In: European journal of organic chemistry
Year: 2020, Issue: 16, Pages: 2384-2388
ISSN:1099-0690
DOI:10.1002/ejoc.201900699
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/ejoc.201900699
Verlag, kostenfrei, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201900699
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Author Notes:Qian Wang, Stephanie Hoffmann, Jasmin Schießl, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
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Summary:Polysubstituted oxazole derivatives are obtained through a regioselective gold-catalyzed reaction of α-alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by alkyne oxidation with a pyridine N-oxide. Acidic conditions ensure that only one of the two carbonyl oxygen atoms in these intermediates selectively cyclizes to the products in excellent yields.
Item Description:Gesehen am 18.05.2020
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.201900699