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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...

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Autores principales: Dethe, Dattatraya H., Beeralingappa, Nagabhushana C., Das, Saikat, Nirpal, Appasaheb K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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