Issue 20, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regioselective SN2 opening of α,β-ethylenic epoxides by RLi–BF3 combination

Alexandre Alexakis,*a   Emmanuel Vrancken,b   Pierre Mangeneyb  and  Fabrice Chemlab  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, Genève 4
E-mail: alexandre.alexakis@chiorg.unige.ch
Fax: Fax (int.) + 41 22 328 73 96
Tel: Tel. + 41 22 702 65 22

b Laboratoire de Chimie des Organoéléments, UMR 7611, Université Pierre et Marie Curie, Cedex 05, 4 place Jussieu, Paris, France

Abstract

Organolithium reagents effect a regioselective SN2 nucleophilic cleavage of α,β-ethylenic epoxides only when BF3·Et2O is added. The reaction works with a variety of RLi reagents and with cyclic as well as acyclic epoxides.

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Article information

DOI
https://doi.org/10.1039/B005472K
Article type
Communication
Submitted
07 Jul 2000
Accepted
18 Sep 2000
First published
02 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3352-3353

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Regioselective SN2 opening of α,β-ethylenic epoxides by RLi–BF3 combination

A. Alexakis, E. Vrancken, P. Mangeney and F. Chemla, J. Chem. Soc., Perkin Trans. 1, 2000, 3352 DOI: 10.1039/B005472K

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