title: Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks.
abstract: The cross metathesis of 1,2-epoxy-5-hexene (1) with methyl acrylate and acrylonitrile was investigated as an entry to the synthesis of polyfunctional compounds. The resulting cross metathesis products were hydrogenated in a tandem fashion employing the residual ruthenium from the metathesis step as the hydrogenation catalyst. Interestingly, the epoxide ring remained unreactive toward this hydrogenation method. The saturated compound resulting from the cross metathesis of 1 with methyl acrylate was transformed by means of nucleophilic ring-opening of the epoxide to furnish a diol, an alkoxy alcohol and an amino alcohol in high yields.
authors.affiliation: Université Frères Mentouri Constantine, Department of Chemistry, Laboratory of Therapeutic Substances Obtention (LOST), Chaabet Ersas Campus, 25000 Constantine, Algeria ; UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Meriem K
authors.initials: MK
authors.lastname: Abderrezak
authors.affiliation: UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France ; Charles University in Prague, Faculty of Science, Department of Physical and Macromolecular Chemistry, Hlavova 2030, CZ-128 40 Prague, Czech Republic.
authors.forename: Kristýna
authors.initials: K
authors.lastname: Šichová
authors.affiliation: UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France ; Faculty of Chemistry, University of Seville, E-41012 Seville, Spain.
authors.forename: Nancy
authors.initials: N
authors.lastname: Dominguez-Boblett
authors.affiliation: UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Antoine
authors.initials: A
authors.lastname: Dupé
authors.affiliation: Université Frères Mentouri Constantine, Department of Chemistry, Laboratory of Therapeutic Substances Obtention (LOST), Chaabet Ersas Campus, 25000 Constantine, Algeria.
authors.forename: Zahia
authors.initials: Z
authors.lastname: Kabouche
authors.affiliation: UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Christian
authors.initials: C
authors.lastname: Bruneau
authors.affiliation: UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France.
authors.forename: Cédric
authors.initials: C
authors.lastname: Fischmeister
keywords: cross metathesis; epoxide; ruthenium catalysts; tandem reactions