Issue 20, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

Alexandre Alexakis,*a   Emmanuel Vranckenb  and  Pierre Mangeneyb  

* 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

Cyclooctene oxide 1, cycloocta-1,3-diene oxide 4, and cycloocta-1,5-diene oxide 7 react with organolithium reagents by nucleophilic opening or α- or β-deprotonation. The addition of BF3·Et2O affects the course of the reaction, and also strongly accelerates it. If (−)-sparteine is present, a moderate to high asymmetric induction is obtained.

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Article information

DOI
https://doi.org/10.1039/B005474G
Article type
Communication
Submitted
07 Jul 2000
Accepted
18 Sep 2000
First published
02 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3354-3355

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Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

A. Alexakis, E. Vrancken and P. Mangeney, J. Chem. Soc., Perkin Trans. 1, 2000, 3354 DOI: 10.1039/B005474G

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