Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans

Producción Científica

Detalhes bibliográficos
Autores: Díez Poza, Carlos, Barbero Pérez, María Asunción
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Recursos:Universidad de Valladolid
Repositorio:UVaDOC. Repositorio Documental de la Universidad de Valladolid
OAI Identifier:oai:uvadoc.uva.es:10324/59213
Acesso em linha:https://doi.org/10.3390/molecules26237386
https://uvadoc.uva.es/handle/10324/59213
Access Level:acceso abierto
Palavra-chave:Química orgánica
Organic chemistry
Tetrahydropyrans
Tetrahydrofurans
Cyclization
Epoxysilyl alcohols
Side reaction
Tandem process
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spelling Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyransDíez Poza, CarlosBarbero Pérez, María AsunciónQuímica orgánicaOrganic chemistryTetrahydropyransTetrahydrofuransCyclizationEpoxysilyl alcoholsSide reactionTandem processProducción CientíficaThe regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The 5-exo opening being preferred vs. the 6-endo mode, according to Baldwin rules, the use of silyl-substituted oxiranes has been reported as a possible method to favor the 6-endo cyclization. However, there is a need for a detailed study on the different factors (structural factors, catalyst nature or conditions) that influence this process. In this paper, the acid-catalyzed cyclization of epoxysilyl alcohols was studied, focusing on the effect of substituents and reaction conditions on the outcome of the process. Two types of heterocycles (tetrahydrofurans or tetrahydropyrans) were selectively obtained depending on the structure of the initial epoxysilyl alcohol. Interestingly, cyclization of hindered epoxysilyl alcohols mainly proceeds through an unexpected side reaction, which implies a previous isomerization to an aldehyde. A mechanistic proposal for the formation of the different products is presented.Junta de Castilla y León - (Project VA294-P18)Fondo Social Europeo y Junta de Castilla y León - (Grant Q4718001C)junMDPI2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://doi.org/10.3390/molecules26237386https://uvadoc.uva.es/handle/10324/59213reponame:UVaDOC. Repositorio Documental de la Universidad de Valladolidinstname:Universidad de ValladolidIngléshttps://www.mdpi.com/1420-3049/26/23/7386info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/oai:uvadoc.uva.es:10324/592132026-06-13T12:44:47Z
dc.title.none.fl_str_mv Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
title Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
spellingShingle Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
Díez Poza, Carlos
Química orgánica
Organic chemistry
Tetrahydropyrans
Tetrahydrofurans
Cyclization
Epoxysilyl alcohols
Side reaction
Tandem process
title_short Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
title_full Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
title_fullStr Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
title_full_unstemmed Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
title_sort Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
dc.creator.none.fl_str_mv Díez Poza, Carlos
Barbero Pérez, María Asunción
author Díez Poza, Carlos
author_facet Díez Poza, Carlos
Barbero Pérez, María Asunción
author_role author
author2 Barbero Pérez, María Asunción
author2_role author
dc.subject.none.fl_str_mv Química orgánica
Organic chemistry
Tetrahydropyrans
Tetrahydrofurans
Cyclization
Epoxysilyl alcohols
Side reaction
Tandem process
topic Química orgánica
Organic chemistry
Tetrahydropyrans
Tetrahydrofurans
Cyclization
Epoxysilyl alcohols
Side reaction
Tandem process
description Producción Científica
publishDate 2021
dc.date.none.fl_str_mv 2021
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/molecules26237386
https://uvadoc.uva.es/handle/10324/59213
url https://doi.org/10.3390/molecules26237386
https://uvadoc.uva.es/handle/10324/59213
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://www.mdpi.com/1420-3049/26/23/7386
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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