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Issue 5, 2015
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Copper-catalyzed stereoselective oxytrifluoromethylation of propargyl amides for the construction of oxazolines

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Abstract

The copper-catalyzed stereoselective oxytrifluoromethylation of terminal propargyl amides took place readily in the presence of Togni's reagent under mild conditions, giving the corresponding trifluoromethylated oxazoline derivatives in moderate to good yields. Using CuBr as catalyst, the E-isomer was obtained as major product. However, the formation of Z-isomer with excellent stereoselectivity was also achieved while Cu(CH3CN)4PF6 was used. Plausible pathways are proposed to account for the excellent stereoselectivity of the reaction.

Graphical abstract: Copper-catalyzed stereoselective oxytrifluoromethylation of propargyl amides for the construction of oxazolines

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Publication details

The article was received on 05 Feb 2015, accepted on 09 Mar 2015 and first published on 13 Mar 2015


Article type: Research Article
DOI: 10.1039/C5QO00044K
Citation: Org. Chem. Front., 2015,2, 542-547
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    Copper-catalyzed stereoselective oxytrifluoromethylation of propargyl amides for the construction of oxazolines

    Y. Wang, M. Jiang and J. Liu, Org. Chem. Front., 2015, 2, 542
    DOI: 10.1039/C5QO00044K

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