Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates

We report a method for the base-mediated transformation of ether-tethered acrylic ester-based cyclic carbonates into functionalized cyclic acetals. The protocol builds on the use of hydroxyalkyl-substituted cyclic carbonates that undergo an oxa-Michael addition reaction in the presence of alkyl prop...

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Detalhes bibliográficos
Autores: Kulbacka, Natalia, Shi, Wangyu, Guillaume, Sophie M., Carpentier, Jean-François, Benet-Buchholz, Jordi, Kleij, Arjan W.
Formato: artículo
Fecha de publicación:2025
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/488972
Acesso em linha:http://hdl.handle.net/2072/488972
https://doi.org/10.1002/adsc.70248
Access Level:acceso abierto
Palavra-chave:Química
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spelling Domino Synthesis of Functionalized Cyclic Acetals From Organic CarbonatesKulbacka, NataliaShi, WangyuGuillaume, Sophie M.Carpentier, Jean-FrançoisBenet-Buchholz, JordiKleij, Arjan W.Química54We report a method for the base-mediated transformation of ether-tethered acrylic ester-based cyclic carbonates into functionalized cyclic acetals. The protocol builds on the use of hydroxyalkyl-substituted cyclic carbonates that undergo an oxa-Michael addition reaction in the presence of alkyl propiolates thereby forging (E)-configured acrylic ether intermediates. The scope of the reaction involves the use of both five- and six-membered cyclic carbonates, and correspondingly, both five- and six-membered cyclic acetals can be prepared. The amount of reagents, the purification method, and the type of ester substrate all contribute to the efficiency of the transformation. Mechanistic control reactions point at the intermediacy of an alkoxide that induces an intramolecular Michael addition onto the acrylic double bond following alkoxide-mediated formation of both an alcohol and ester in the final product. These functional groups, among others, further enable easy diversification of acetal-based synthons.info:eu-repo/semantics/publishedVersionWiley2025info:eu-repo/semantics/article11 p.application/pdfhttp://hdl.handle.net/2072/488972https://doi.org/10.1002/adsc.70248RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésCERCA Program/Generalitat de CatalunyaICREA FoundationMICINN (PID2023-149295NB-I00 and Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)AGAUR (2021-SGR-00853)European Union's Horizon 2020 research and innovation program for further support through Marie Skłodowska-Curie Grant Agreement No. 101073223 (D-Carbonize project)Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2072/4889722026-05-29T05:05:01Z
dc.title.none.fl_str_mv Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
title Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
spellingShingle Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
Kulbacka, Natalia
Química
54
title_short Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
title_full Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
title_fullStr Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
title_full_unstemmed Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
title_sort Domino Synthesis of Functionalized Cyclic Acetals From Organic Carbonates
dc.creator.none.fl_str_mv Kulbacka, Natalia
Shi, Wangyu
Guillaume, Sophie M.
Carpentier, Jean-François
Benet-Buchholz, Jordi
Kleij, Arjan W.
author Kulbacka, Natalia
author_facet Kulbacka, Natalia
Shi, Wangyu
Guillaume, Sophie M.
Carpentier, Jean-François
Benet-Buchholz, Jordi
Kleij, Arjan W.
author_role author
author2 Shi, Wangyu
Guillaume, Sophie M.
Carpentier, Jean-François
Benet-Buchholz, Jordi
Kleij, Arjan W.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Química
54
topic Química
54
description We report a method for the base-mediated transformation of ether-tethered acrylic ester-based cyclic carbonates into functionalized cyclic acetals. The protocol builds on the use of hydroxyalkyl-substituted cyclic carbonates that undergo an oxa-Michael addition reaction in the presence of alkyl propiolates thereby forging (E)-configured acrylic ether intermediates. The scope of the reaction involves the use of both five- and six-membered cyclic carbonates, and correspondingly, both five- and six-membered cyclic acetals can be prepared. The amount of reagents, the purification method, and the type of ester substrate all contribute to the efficiency of the transformation. Mechanistic control reactions point at the intermediacy of an alkoxide that induces an intramolecular Michael addition onto the acrylic double bond following alkoxide-mediated formation of both an alcohol and ester in the final product. These functional groups, among others, further enable easy diversification of acetal-based synthons.
publishDate 2025
dc.date.none.fl_str_mv 2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/488972
https://doi.org/10.1002/adsc.70248
url http://hdl.handle.net/2072/488972
https://doi.org/10.1002/adsc.70248
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CERCA Program/Generalitat de Catalunya
ICREA Foundation
MICINN (PID2023-149295NB-I00 and Severo Ochoa Excellence Accreditation 2020–2023 CEX2019-000925-S)
AGAUR (2021-SGR-00853)
European Union's Horizon 2020 research and innovation program for further support through Marie Skłodowska-Curie Grant Agreement No. 101073223 (D-Carbonize project)
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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