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

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

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 2 , 2012

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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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Article Details

Year: 2012
Page: [96 - 100]
Pages: 5
DOI: 10.2174/157017812800221681

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