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

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

Volume: 9 Issue: 2

Author(s): Heithem Abda, Kaiss Aouadi, David Gueyrard, Jean-Pierre Praly and Moncef Msaddek

Affiliation:

Keywords: 1,3-dipolar cycloaddition, allylic alcohols, aryl nitrile oxides, isoxazoline, NOESY, isoxazolines, oxygen, chlorides, hydroximoyl, phenyl

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.

Cite this article as:

Abda Heithem, Aouadi Kaiss, Gueyrard David, Praly Jean-Pierre and Msaddek Moncef, Study of the Regio- and Stereoselectivity of [3+2] Cycloaddition of Nitrile Oxides to Various Racemic 3-acyloxy and 3-hydroxybut-1-enes, Letters in Organic Chemistry 2012; 9 (2) . https://dx.doi.org/10.2174/157017812800221681