Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

Meriem K. Abderrezak (1) , Kristýna Šichová , Nancy Dominguez-Boblett (2, 3) , Antoine Dupé (2) , Zahia Kabouche (1) , Christian Bruneau (2) , Cédric Fischmeister (2)

1 UMC - Université frères Mentouri Constantine I
2 ISCR - Institut des Sciences Chimiques de Rennes
3 Universidad de Sevilla / University of Sevilla

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

Keywords: cross metathesis; epoxide; ruthenium catalysts; tandem reactions

Domains: Chemical Sciences

Meriem K. Abderrezak, Kristýna Šichová, Nancy Dominguez-Boblett, Antoine Dupé, Zahia Kabouche, et al.. Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks. Beilstein Journal of Organic Chemistry, 2015, 11, pp.1876--1880. ⟨10.3762/bjoc.11.201⟩. ⟨hal-01254823⟩