Generic placeholder image

Letters in Organic Chemistry

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

DOI: 10.2174/157017812800221681

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

Page: [96 - 100] Pages: 5

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

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