Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid-Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
dc.contributor.author | Prieto Aretxabaleta, Liher | |
dc.contributor.author | Reyes Martín, Efraim | |
dc.contributor.author | Uria Pujana, Uxue | |
dc.contributor.author | Carrillo Fernández, María Luisa | |
dc.contributor.author | Vicario Hernando, José Luis | |
dc.date.accessioned | 2023-09-18T16:55:57Z | |
dc.date.available | 2023-09-18T16:55:57Z | |
dc.date.issued | 2023-07 | |
dc.identifier.citation | Asian Journal of Organic Chemistry 12(7) : (2023) // Article ID e202300163 | es_ES |
dc.identifier.issn | 2193-5807 | |
dc.identifier.issn | 2193-5815 | |
dc.identifier.uri | http://hdl.handle.net/10810/62585 | |
dc.description.abstract | This work presents the desymmetrization of oxabenzonorbornadienes through the (3+2) cycloaddition reaction with hydrazones using a chiral Brønsted acid such as a BINOL-derived phosphoramide. This chiral acid catalyst appears as the most effective mediator for the activation of the hydrazone via hydrazonium cation that reacts in a (3+2) fashion with the oxabenzonorbornadiene as the olefinic counterpart. Under the optimized conditions, the reaction provided selectively exo cycloaddition products in satisfactory yields and moderate stereoselectivities. The scope of the reaction was explored displaying 21 examples of these highly functionalized tetrahydroepoxybenzoindazole compounds. A reaction mechanism is proposed to explain the outcome of the reaction. | es_ES |
dc.description.sponsorship | Grant PID2020-118422GB-I00 funded by MCIN/AEI/10.13039/501100011033 and by “ESF Investing in your future” is gratefully acknowledged. Financial support by the the Basque Government (Grupos IT1558-22) is also gratefully acknowledged. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2020-118422GB-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ | * |
dc.title | Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid-Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2023 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. | es_ES |
dc.rights.holder | Atribución-NoComercial-SinDerivadas 3.0 España | * |
dc.relation.publisherversion | https://onlinelibrary.wiley.com/doi/full/10.1002/ajoc.202300163 | es_ES |
dc.identifier.doi | 10.1002/ajoc.202300163 | |
dc.departamentoes | Química Orgánica e Inorgánica | es_ES |
dc.departamentoeu | Kimika Organikoa eta Ez-Organikoa | es_ES |
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Except where otherwise noted, this item's license is described as © 2023 The Authors. Asian Journal of Organic Chemistry published by Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.