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Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
The Z-selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z-isomer (typically >95%) and yields of up to 88% for a variety of allylic substituents. This in...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4339074/ https://www.ncbi.nlm.nih.gov/pubmed/25722847 http://dx.doi.org/10.1039/c3sc52806e |
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author | Quigley, Brendan L. Grubbs, Robert H. |
author_facet | Quigley, Brendan L. Grubbs, Robert H. |
author_sort | Quigley, Brendan L. |
collection | PubMed |
description | The Z-selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z-isomer (typically >95%) and yields of up to 88% for a variety of allylic substituents. This includes the first synthesis of Z-α,β-unsaturated acetals by cross metathesis and their elaboration to Z-α,β-unsaturated aldehydes. In addition, the reaction is tolerant of a variety of cross partners, varying in functionality and steric profile. |
format | Online Article Text |
id | pubmed-4339074 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-43390742015-02-24 Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins Quigley, Brendan L. Grubbs, Robert H. Chem Sci Chemistry The Z-selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z-isomer (typically >95%) and yields of up to 88% for a variety of allylic substituents. This includes the first synthesis of Z-α,β-unsaturated acetals by cross metathesis and their elaboration to Z-α,β-unsaturated aldehydes. In addition, the reaction is tolerant of a variety of cross partners, varying in functionality and steric profile. Royal Society of Chemistry 2014-02-23 2013-11-21 /pmc/articles/PMC4339074/ /pubmed/25722847 http://dx.doi.org/10.1039/c3sc52806e Text en This journal is © The Royal Society of Chemistry 2013 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Quigley, Brendan L. Grubbs, Robert H. Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins |
title | Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
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title_full | Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
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title_fullStr | Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
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title_full_unstemmed | Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
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title_short | Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins
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title_sort | ruthenium-catalysed z-selective cross metathesis of allylic-substituted olefins |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4339074/ https://www.ncbi.nlm.nih.gov/pubmed/25722847 http://dx.doi.org/10.1039/c3sc52806e |
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