The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis

In this study we have investigated computationally the origin of the cis–trans selectivity in the Ru-catalyzed cross metathesis (CM) of a prototype monosubstituted olefin, i.e., propene. Our calculations suggest that the origin of the preferential formation of trans-olefins is in the product release...

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Detalles Bibliográficos
Autores principales: Bahri-Laleh, Naeimeh, Credendino, Raffaele, Cavallo, Luigi
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028549/
https://www.ncbi.nlm.nih.gov/pubmed/21286393
http://dx.doi.org/10.3762/bjoc.7.7
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author Bahri-Laleh, Naeimeh
Credendino, Raffaele
Cavallo, Luigi
author_facet Bahri-Laleh, Naeimeh
Credendino, Raffaele
Cavallo, Luigi
author_sort Bahri-Laleh, Naeimeh
collection PubMed
description In this study we have investigated computationally the origin of the cis–trans selectivity in the Ru-catalyzed cross metathesis (CM) of a prototype monosubstituted olefin, i.e., propene. Our calculations suggest that the origin of the preferential formation of trans-olefins is in the product release step, which prevents the initially formed cis-olefin from escaping the metal, and returns it to the reaction pool until the trans-olefin is formed.
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spelling pubmed-30285492011-01-31 The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis Bahri-Laleh, Naeimeh Credendino, Raffaele Cavallo, Luigi Beilstein J Org Chem Letter In this study we have investigated computationally the origin of the cis–trans selectivity in the Ru-catalyzed cross metathesis (CM) of a prototype monosubstituted olefin, i.e., propene. Our calculations suggest that the origin of the preferential formation of trans-olefins is in the product release step, which prevents the initially formed cis-olefin from escaping the metal, and returns it to the reaction pool until the trans-olefin is formed. Beilstein-Institut 2011-01-11 /pmc/articles/PMC3028549/ /pubmed/21286393 http://dx.doi.org/10.3762/bjoc.7.7 Text en Copyright © 2011, Bahri-Laleh et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Bahri-Laleh, Naeimeh
Credendino, Raffaele
Cavallo, Luigi
The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title_full The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title_fullStr The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title_full_unstemmed The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title_short The intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
title_sort intriguing modeling of cis–trans selectivity in ruthenium-catalyzed olefin metathesis
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028549/
https://www.ncbi.nlm.nih.gov/pubmed/21286393
http://dx.doi.org/10.3762/bjoc.7.7
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