Abstract

GUCMA, Mirosław; GOłęBIEWSKI, W. Marek  and  MICHALCZYK, Alicja K.. Enantioselective Synthesis of Isoxazolecarboxamides and their Fungicidal Activity. J. Mex. Chem. Soc [online]. 2015, vol.59, n.2, pp.161-172. ISSN 1870-249X.

A series of new 3-substituted isoxazolecarboxamides have been prepared from aldehydes. The key step was a 1,3-dipolar cycloaddition reaction of nitrile oxides to α,β-unsaturated esters and amides. The cycloadditions to amides were mediated by chiral ligands and several products displayed excellent enantioselectivities. Some of the title compounds exhibited good fungicidal activities against Alternaria alternata, Botrytis cinerea, Fusarium culmorum, Phytophthora cactorum, and Rhizoctonia solani strains.

Keywords : cycloaddition; isoxazole derivatives; regioselectivity; enantioselectivity; fungicides.