Issue 13, 2000
From the journal:

Chemical Communications

Switching stereocontrol in the high pressure-induced hetero-Diels–Alder reaction

Hashim Al-Badri,a   Noël Collignon,b   Jacques Maddaluno*a  and  Serge Massonc  

* Corresponding authors

a Laboratoire des Fonctions Azotées et Oxygénées Complexes de l’IRCOF, UPRES-A 6014 CNRS, Université de Rouen, 76821, Mont-Saint-Aignan Cedex, France.
E-mail: jmaddalu@crihan.fr

b Laboratoire d’Hétérochimie Organique de l’IRCOF, UPRES-A 6014 CNRS, INSA de Rouen, Place E. Blondel, BP 08, 76131, Mont-Saint-Aignan Cedex, France

c Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS, Université de Caen et ISMRA, 6 Boulevard du Maréchal Juin, 14050, Caen Cedex, France

Abstract

The formation of a transient Michael adduct, triggering an in-situ isomerization of the heterodiene, is postulated to explain the reversal of the diastereoselectivity of high pressure-promoted hetero-Diels–Alder reactions carried out in the presence of pyridine.

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Article information

DOI
https://doi.org/10.1039/B003060K
Article type
Communication
Submitted
17 Apr 2000
Accepted
19 May 2000
First published
14 Jun 2000

Chem. Commun., 2000, 1191-1192

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Switching stereocontrol in the high pressure-induced hetero-Diels–Alder reaction

H. Al-Badri, N. Collignon, J. Maddaluno and S. Masson, Chem. Commun., 2000, 1191 DOI: 10.1039/B003060K

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