Issue 17, 2009
From the journal:

Organic & Biomolecular Chemistry

Synthesis of functionalized Morita–Baylis–Hillman adducts by a conjugate addition–elimination sequence†

Rémi Aouzala  and  Joëlle Prunet*a  

* Corresponding authors

a Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, France
E-mail: joelle.prunet@polytechnique.fr
Fax: +33 1 69 33 59 72
Tel: +33 1 69 33 59 79

Abstract

We have developed a new conjugate addition–elimination sequence for the diastereoselective synthesis of protected allylic syn 1,3-diols which are Morita–Baylis–Hillman adducts. The synthesis of the substrates involves a challenging cross-metathesis reaction that leads to hindered trisubstituted olefins.

Graphical abstract: Synthesis of functionalized Morita–Baylis–Hillman adducts by a conjugate addition–elimination sequence

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Article information

DOI
https://doi.org/10.1039/B907373F
Article type
Paper
Submitted
14 Apr 2009
Accepted
08 Jun 2009
First published
10 Jul 2009

Org. Biomol. Chem., 2009,7, 3594-3598

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Synthesis of functionalized Morita–Baylis–Hillman adducts by a conjugate addition–elimination sequence

R. Aouzal and J. Prunet, Org. Biomol. Chem., 2009, 7, 3594 DOI: 10.1039/B907373F

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