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Indium-Catalyzed Synthesis of Benzannulated Spiroketals by Intramolecular Double Hydroalkoxylation of Ortho-(Hydroxyalkynyl)Benzyl Alcohols
dc.contributor.author | Pérez Guevara, Raquel | |
dc.contributor.author | Sarandeses, Luis A. | |
dc.contributor.author | Martínez, Montserrat | |
dc.contributor.author | Pérez Sestelo, José | |
dc.date.accessioned | 2024-01-25T20:09:43Z | |
dc.date.issued | 2022-10-31 | |
dc.identifier.citation | Pérez-Guevara, R., Sarandeses, L. A., Martínez, M. M., & Sestelo, J. P. (2022). Indium-catalyzed synthesis of benzannulated spiroketals by intramolecular double hydroalkoxylation of ortho-(hydroxyalkynyl)benzyl alcohols. Organic Chemistry Frontiers, 9(24), 6894-6901. https://doi.org/10.1039/D2QO01600A | es_ES |
dc.identifier.issn | 2052-4129 | |
dc.identifier.uri | http://hdl.handle.net/2183/35172 | |
dc.description.abstract | [Abstract] The novel indium-catalyzed synthesis of benzannulated spiroketals by a double intramolecular hydroalkoxylation reaction of o-(hydroxyalkynyl)benzyl alcohols is reported. The reaction proceeds under mild reaction conditions using a low catalyst loading of indium triiodide (2–5 mol%) with a variety of benzyl and homobenzyl alcohols, allowing the regioselective synthesis of a set of naturally occurring and new benzannulated spiroketals (5,5-, 5,6-, 5,7-, 6,6- and 6,7-) in good yields. The synthetic transformation involves the indium(III)-catalyzed electrophilic alkyne activation followed by the regioselective intramolecular hydroalkoxylation reaction. The method is the first example of spiroketal synthesis using main group catalysis representing an economical alternative to precious transition metals. In addition, it provides a complementary strategy for the regioselective synthesis of spiroketals and spiroaminals. | es_ES |
dc.description.sponsorship | We thank the Ministerio de Ciencia, Innovación y Universidades (Spain, PGC2018-097792-B-I00 and PID2021-122335NB-I00), Xunta de Galicia (GRC2018/039 and GRC2022/039), and EDRF funds for financial and human support. R. P-G. thanks Xunta de Galicia for a predoctoral fellowship | es_ES |
dc.description.sponsorship | Xunta de Galicia; GRC2018/039 | es_ES |
dc.description.sponsorship | Xunta de Galicia; GRC2022/039 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Royal Society of Chemistry (Gran Bretaña) | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-097792-B-I00/ES/EL INDIO COMO HERRAMIENTA SINTETICA EN REACCIONES DE ACOPLAMIENTO Y EN CATALISIS/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-122335NB-I00/ES/CATALISIS CON COMPLEJOS METALICOS Y ORGANOMETALICOS DEL GRUPO 13/ | es_ES |
dc.relation.uri | https://doi.org/10.1039/D2QO01600A | es_ES |
dc.rights | © the Partner Organisations 2022 | es_ES |
dc.title | Indium-Catalyzed Synthesis of Benzannulated Spiroketals by Intramolecular Double Hydroalkoxylation of Ortho-(Hydroxyalkynyl)Benzyl Alcohols | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/embargoedAccess | es_ES |
dc.date.embargoEndDate | 9999-99-99 | es_ES |
dc.date.embargoLift | 10007-06-07 | |
UDC.journalTitle | Organic Chemistry Frontiers | es_ES |
UDC.volume | 9 (2022) | es_ES |
UDC.issue | 24 (21 December) | es_ES |
UDC.startPage | 6894 | es_ES |
UDC.endPage | 6901 | es_ES |
dc.identifier.doi | 10.1039/D2QO01600A |