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Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes
Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed via isomerization followed by C(allyl)–H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179449/ https://www.ncbi.nlm.nih.gov/pubmed/34163699 http://dx.doi.org/10.1039/d0sc06845d |
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author | Dethe, Dattatraya H. Beeralingappa, Nagabhushana C. Das, Saikat Nirpal, Appasaheb K. |
author_facet | Dethe, Dattatraya H. Beeralingappa, Nagabhushana C. Das, Saikat Nirpal, Appasaheb K. |
author_sort | Dethe, Dattatraya H. |
collection | PubMed |
description | Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed via isomerization followed by C(allyl)–H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent regio- and diastereoselectivity ensure universality of the reaction. In addition, the unique power of this reaction was illustrated by performing the Diels–Alder reaction, and enantioselective synthesis of highly functionalized cyclohexenone and piperidine and finally synthetic utility was further demonstrated by the efficient synthesis of norpyrenophorin, an antifungal agent. |
format | Online Article Text |
id | pubmed-8179449 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81794492021-06-22 Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes Dethe, Dattatraya H. Beeralingappa, Nagabhushana C. Das, Saikat Nirpal, Appasaheb K. Chem Sci Chemistry Ru-catalysed oxidative coupling of allylsilanes and allyl esters with activated olefins has been developed via isomerization followed by C(allyl)–H activation providing efficient access to stereodefined 1,3-dienes in excellent yields. Mild reaction conditions, less expensive catalysts, and excellent regio- and diastereoselectivity ensure universality of the reaction. In addition, the unique power of this reaction was illustrated by performing the Diels–Alder reaction, and enantioselective synthesis of highly functionalized cyclohexenone and piperidine and finally synthetic utility was further demonstrated by the efficient synthesis of norpyrenophorin, an antifungal agent. The Royal Society of Chemistry 2021-02-02 /pmc/articles/PMC8179449/ /pubmed/34163699 http://dx.doi.org/10.1039/d0sc06845d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Dethe, Dattatraya H. Beeralingappa, Nagabhushana C. Das, Saikat Nirpal, Appasaheb K. Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title | Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title_full | Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title_fullStr | Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title_full_unstemmed | Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title_short | Ruthenium-catalyzed formal sp(3) C–H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
title_sort | ruthenium-catalyzed formal sp(3) c–h activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179449/ https://www.ncbi.nlm.nih.gov/pubmed/34163699 http://dx.doi.org/10.1039/d0sc06845d |
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