Issue 5, 2015

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
05 Feb 2015
Accepted
09 Mar 2015
First published
13 Mar 2015

Org. Chem. Front., 2015,2, 542-547

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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