Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones

Cyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cycliz...

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Authors: Garre Hernández, María Soledad|||0000-0002-7075-3548, Otárola Tejada, Guillermo Germán|||0000-0003-1367-3127, Merino Marcos, Estíbaliz|||0000-0002-2960-5404, Sucunza Sáenz, David|||0000-0002-3307-4204, Aguilar, Enrique, Quirós López, María Teresa|||0000-0002-1552-0901, Vaquero López, Juan José|||0000-0002-3820-9673, García García, Patricia|||0000-0003-3671-5828
Format: article
Publication Date:2023
Country:España
Institution:Universidad de Alcalá (UAH)
Repository:e_Buah Biblioteca Digital Universidad de Alcalá
Language:English
OAI Identifier:oai:ebuah.uah.es:10017/59222
Online Access:http://hdl.handle.net/10017/59222
https://dx.doi.org/10.1039/D3OB00051F
Access Level:Open access
Keyword:Química
Chemistry
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spelling Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridonesGarre Hernández, María Soledad|||0000-0002-7075-3548Otárola Tejada, Guillermo Germán|||0000-0003-1367-3127Merino Marcos, Estíbaliz|||0000-0002-2960-5404Sucunza Sáenz, David|||0000-0002-3307-4204Aguilar, EnriqueQuirós López, María Teresa|||0000-0002-1552-0901Vaquero López, Juan José|||0000-0002-3820-9673García García, Patricia|||0000-0003-3671-5828QuímicaChemistryCyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cyclization of related alcohols and acids, is supported by DFT calculations.Ministerio de Ciencia e InnovaciónInstituto de Salud Carlos IIIComunidad de Madrid20232023-03-01journal articlehttp://purl.org/coar/resource_type/c_6501NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10017/59222https://dx.doi.org/10.1039/D3OB00051Freponame:e_Buah Biblioteca Digital Universidad de Alcaláinstname:Universidad de Alcalá (UAH)InglésengMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available PID2020-115128RB-I00ISCIII Not available RICORS2040%2FRD21%2F 0005%2F0016Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available 2018-T1%2FIND-10054Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available Not available ESopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-ShareAlike 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-sa/4.0/info:eu-repo/semantics/openAccessoai:ebuah.uah.es:10017/592222026-06-18T11:13:07Z
dc.title.none.fl_str_mv Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
title Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
spellingShingle Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
Garre Hernández, María Soledad|||0000-0002-7075-3548
Química
Chemistry
title_short Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
title_full Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
title_fullStr Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
title_full_unstemmed Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
title_sort Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones
dc.creator.none.fl_str_mv Garre Hernández, María Soledad|||0000-0002-7075-3548
Otárola Tejada, Guillermo Germán|||0000-0003-1367-3127
Merino Marcos, Estíbaliz|||0000-0002-2960-5404
Sucunza Sáenz, David|||0000-0002-3307-4204
Aguilar, Enrique
Quirós López, María Teresa|||0000-0002-1552-0901
Vaquero López, Juan José|||0000-0002-3820-9673
García García, Patricia|||0000-0003-3671-5828
author Garre Hernández, María Soledad|||0000-0002-7075-3548
author_facet Garre Hernández, María Soledad|||0000-0002-7075-3548
Otárola Tejada, Guillermo Germán|||0000-0003-1367-3127
Merino Marcos, Estíbaliz|||0000-0002-2960-5404
Sucunza Sáenz, David|||0000-0002-3307-4204
Aguilar, Enrique
Quirós López, María Teresa|||0000-0002-1552-0901
Vaquero López, Juan José|||0000-0002-3820-9673
García García, Patricia|||0000-0003-3671-5828
author_role author
author2 Otárola Tejada, Guillermo Germán|||0000-0003-1367-3127
Merino Marcos, Estíbaliz|||0000-0002-2960-5404
Sucunza Sáenz, David|||0000-0002-3307-4204
Aguilar, Enrique
Quirós López, María Teresa|||0000-0002-1552-0901
Vaquero López, Juan José|||0000-0002-3820-9673
García García, Patricia|||0000-0003-3671-5828
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
Chemistry
topic Química
Chemistry
description Cyclobutane-fused dihydropyridones can be efficiently synthesized by a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes bearing an appended amide, which proceeds under mild conditions. The observed selectivity, which is reversed from that previously observed for the cyclization of related alcohols and acids, is supported by DFT calculations.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-03-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10017/59222
https://dx.doi.org/10.1039/D3OB00051F
url http://hdl.handle.net/10017/59222
https://dx.doi.org/10.1039/D3OB00051F
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available PID2020-115128RB-I00
ISCIII Not available RICORS2040%2FRD21%2F 0005%2F0016
Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available 2018-T1%2FIND-10054
Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available Not available ES
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-ShareAlike 4.0 International
http://creativecommons.org/licenses/by-nc-sa/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-ShareAlike 4.0 International
http://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:e_Buah Biblioteca Digital Universidad de Alcalá
instname:Universidad de Alcalá (UAH)
instname_str Universidad de Alcalá (UAH)
reponame_str e_Buah Biblioteca Digital Universidad de Alcalá
collection e_Buah Biblioteca Digital Universidad de Alcalá
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