Michael A. Schmidt, K. Katipally, Antonio Ramirez
Aug 1, 2012
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron Letters
Abstract
Efforts to prepare ethyl 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylate (1) by developing a regioselective 1,3-dipolar cycloaddition between phenyl nitrile oxide and various 4,4,4-trifluoromethyl crotonates are described. The substitution at the C2-position of crotonate dipolarophile 4 significantly influenced the regiochemistry and yield of the cycloaddition. Enol and enol ether-based crotonates underwent regioselective cycloadditions with phenyl nitrile oxide to provide 4-trifluoromethyl isoxazoles in good yields.