Issue 38, 2005
From the journal:

Chemical Communications

Reversal of facial selectivity in complex Diels–Alder reactions†

Jacques-Alexis Funel,a   Louis Ricardb  and  Joëlle Prunet*a  

* Corresponding authors

a Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, Palaiseau Cedex, France
E-mail: joelle.prunet@polytechnique.fr
Fax: +33 1 69 33 38 51
Tel: +33 1 69 33 48 73

b Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653, Ecole Polytechnique, DCPH, Palaiseau Cedex, France
E-mail: louis.ricard@ polytechnique.fr
Fax: +33 1 69 33 39 90
Tel: +33 1 69 33 45 72

Abstract

A complex Diels–Alder reaction between a semi-cyclic diene with allylic silyloxy substituents and a bromo enone presented an unusual diastereoselectivity: attack of the diene occured on its more hindered face, and this reversal of selectivity was shown to be induced by the presence of a bromo substituent in the dienophile.

Graphical abstract: Reversal of facial selectivity in complex Diels–Alder reactions

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Article information

DOI
https://doi.org/10.1039/B509041E
Article type
Communication
Submitted
27 Jun 2005
Accepted
28 Jul 2005
First published
02 Sep 2005

Chem. Commun., 2005, 4833-4835

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Reversal of facial selectivity in complex Diels–Alder reactions

J. Funel, L. Ricard and J. Prunet, Chem. Commun., 2005, 4833 DOI: 10.1039/B509041E

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