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Study of the Regio- and Stereoselectivity of [3+2] Cycloaddition of Nitrile Oxides to Various Racemic 3-acyloxy and 3-hydroxybut-1-enes

[ Vol. 9 , Issue. 2 ]

Author(s):

Heithem Abda, Kaiss Aouadi, David Gueyrard, Jean-Pierre Praly and Moncef Msaddek   Pages 96 - 100 ( 5 )

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

Affiliation:

Laboratoire de Synthese Heterocyclique et Substances Naturelles, Departement de Chimie, Faculte des Sciences, 5000 Monastir, Tunisia.



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