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

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...

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Main Authors:	Meriem K. Abderrezak, Kristýna Šichová, Nancy Dominguez-Boblett, Antoine Dupé, Zahia Kabouche, Christian Bruneau, Cédric Fischmeister
Format:	Article
Language:	English
Published:	Beilstein-Institut 2015-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cross metathesis epoxide ruthenium catalysts tandem reactions
Online Access:	https://doi.org/10.3762/bjoc.11.201

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spelling	doaj-80162728d6d54435b8336b6559711cab2021-02-02T04:48:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-10-011111876188010.3762/bjoc.11.2011860-5397-11-201Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocksMeriem K. Abderrezak0Kristýna Šichová1Nancy Dominguez-Boblett2Antoine Dupé3Zahia Kabouche4Christian Bruneau5Cédric Fischmeister6Université Frères Mentouri Constantine, Department of Chemistry, Laboratory of Therapeutic Substances Obtention (LOST), Chaabet Ersas Campus, 25000 Constantine, AlgeriaUMR6226 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, FranceUMR6226 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, FranceUMR6226 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, FranceUniversité Frères Mentouri Constantine, Department of Chemistry, Laboratory of Therapeutic Substances Obtention (LOST), Chaabet Ersas Campus, 25000 Constantine, AlgeriaUMR6226 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, FranceUMR6226 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, FranceThe 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.https://doi.org/10.3762/bjoc.11.201cross metathesisepoxideruthenium catalyststandem reactions
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Meriem K. Abderrezak Kristýna Šichová Nancy Dominguez-Boblett Antoine Dupé Zahia Kabouche Christian Bruneau Cédric Fischmeister
spellingShingle	Meriem K. Abderrezak Kristýna Šichová Nancy Dominguez-Boblett Antoine Dupé Zahia Kabouche Christian Bruneau Cédric Fischmeister Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks Beilstein Journal of Organic Chemistry cross metathesis epoxide ruthenium catalysts tandem reactions
author_facet	Meriem K. Abderrezak Kristýna Šichová Nancy Dominguez-Boblett Antoine Dupé Zahia Kabouche Christian Bruneau Cédric Fischmeister
author_sort	Meriem K. Abderrezak
title	Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
title_short	Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
title_full	Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
title_fullStr	Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
title_full_unstemmed	Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
title_sort	cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2015-10-01
description	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.
topic	cross metathesis epoxide ruthenium catalysts tandem reactions
url	https://doi.org/10.3762/bjoc.11.201
work_keys_str_mv	AT meriemkabderrezak crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT kristynasichova crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT nancydominguezboblett crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT antoinedupe crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT zahiakabouche crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT christianbruneau crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks AT cedricfischmeister crossmetathesisofunsaturatedepoxidesforthesynthesisofpolyfunctionalbuildingblocks
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Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

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