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Synthesis 2011(13): 2125-2130  
DOI: 10.1055/s-0030-1260605
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Terpenic Compounds as Renewable Sources of Raw Materials for Cross-Metathesis

Etienne Borréa,b, Trong Hoa Dinha,b, Frédéric Caijo*c, Christophe Crévisy*a,b, Marc Mauduit*a,b
a Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France
Fax: +33(2)23238108; e-Mail: crevisy@ensc-rennes.fr; e-Mail: marc.mauduit@ensc-rennes.fr;
b Université européenne de Bretagne, 5 Boulevard Laënnec, 35000 Rennes, France
c Oméga Cat System, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France
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Publication History

Received 22 March 2011
Publication Date:
26 May 2011 (online)

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Abstract

Dihydromyrcenol is used as a hydrated masked form of citronellene in olefin cross-metathesis reactions in order to solve the selectivity problem that results from the presence of two double bonds in many terpenes. Several ruthenium catalysts are evaluated, with the best, M71-SIPr, utilized in the cross-metathesis of dihydromyrcenol with various olefins affording the expected products in good yields. It is shown that the masked double bond can be regenerated via an acid-catalyzed elimination reaction and the product is then subjected to a further cross-metathesis reaction with a second olefin.

Key words

terpenoids - olefin metathesis - chemoselectivity - agro-resources - dihydromyrcenol