Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways

Producción Científica

Detalles Bibliográficos
Autores: Fernández Peña, Laura, López Hernández, Enol, Sánchez González, Ángel, Barbero Pérez, María Asunción
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/63811
Acceso en línea:https://doi.org/10.3390/molecules28073080
https://uvadoc.uva.es/handle/10324/63811
Access Level:acceso abierto
Palabra clave:Heterocyclic compounds
Compuestos heterocíclicos
Analytical chemistry
Prins cyclization
Oxacycles
2301 Química Analítica
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spelling Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathwaysFernández Peña, LauraLópez Hernández, EnolSánchez González, ÁngelBarbero Pérez, María AsunciónHeterocyclic compoundsCompuestos heterocíclicosAnalytical chemistryPrins cyclizationOxacycles2301 Química AnalíticaProducción CientíficaA convenient regioselective synthesis of allyl- and vinylsilyl alcohols, from a common precursor, was described, by selecting the appropriate reaction conditions. Allyl- and vinylsilyl alcohols were tested in silyl-Prins cyclizations for the preparation of disubstituted oxygenated heterocycles in a one-pot sequential reaction. The methodology was sensitive to the structure of the starting alkenylsilyl alcohol and reaction conditions, with competitive pathways observed (particularly for allylsilyl alcohols), such as Peterson elimination and oxonia-Cope reactions. However, the use of vinylsilyl alcohols allowed the preparation of differently disubstituted cis-2,6-dihydropyrans in moderate to good yields. Computational studies support the proposed mechanism.Junta de Castilla y León - (grant VA294-P18)Ministerio de Ciencia e Innovación - (PID2020-116076RJI00/AEI/10.13039/501100011033)MDPI2023info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.3390/molecules28073080https://uvadoc.uva.es/handle/10324/63811reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://www.mdpi.com/1420-3049/28/7/3080info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/oai:uvadoc.uva.es:10324/638112026-06-13T12:44:47Z
dc.title.none.fl_str_mv Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
title Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
spellingShingle Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
Fernández Peña, Laura
Heterocyclic compounds
Compuestos heterocíclicos
Analytical chemistry
Prins cyclization
Oxacycles
2301 Química Analítica
title_short Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
title_full Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
title_fullStr Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
title_full_unstemmed Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
title_sort Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
dc.creator.none.fl_str_mv Fernández Peña, Laura
López Hernández, Enol
Sánchez González, Ángel
Barbero Pérez, María Asunción
author Fernández Peña, Laura
author_facet Fernández Peña, Laura
López Hernández, Enol
Sánchez González, Ángel
Barbero Pérez, María Asunción
author_role author
author2 López Hernández, Enol
Sánchez González, Ángel
Barbero Pérez, María Asunción
author2_role author
author
author
dc.subject.none.fl_str_mv Heterocyclic compounds
Compuestos heterocíclicos
Analytical chemistry
Prins cyclization
Oxacycles
2301 Química Analítica
topic Heterocyclic compounds
Compuestos heterocíclicos
Analytical chemistry
Prins cyclization
Oxacycles
2301 Química Analítica
description Producción Científica
publishDate 2023
dc.date.none.fl_str_mv 2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://doi.org/10.3390/molecules28073080
https://uvadoc.uva.es/handle/10324/63811
url https://doi.org/10.3390/molecules28073080
https://uvadoc.uva.es/handle/10324/63811
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://www.mdpi.com/1420-3049/28/7/3080
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolid
instname:Universidad de Valladolid
instname_str Universidad de Valladolid
reponame_str UVaDOC. Repositorio Documental de la Universidad de Valladolid
collection UVaDOC. Repositorio Documental de la Universidad de Valladolid
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,30478

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