Abstract
1,3-Dipolar cycloadditions of aryl nitrile oxides 2d-f to various racemic 3-hydroxy- and 3-acyloxy-but-1-enes 1a-c proceeded with complete regioselectivity to afford the corresponding 3,5-disubstituted isoxazolines in good yields. The steric and/or electronic effect of an acyloxy group at the allylic position on the stereoselectivity has been studied. Keywords: 1,3-dipolar cycloaddition, allylic alcohols, aryl nitrile oxides, isoxazoline, NOESY, isoxazolines, oxygen, chlorides, hydroximoyl, phenyl
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