Stereo- and Regioselective [3+3] Annulation Reaction Catalyzed by Ytterbium: Synthesis of Bicyclic 1,4-Dihydropyridines.
dc.contributor.author | Del Corte Solaguren-Beascoa, Xabier | |
dc.contributor.author | López Francés, Adrián | |
dc.contributor.author | Martínez de Marigorta Izaga, Edorta | |
dc.contributor.author | Palacios Gambra, Francisco Javier | |
dc.contributor.author | Vicario Hernando, Javier | |
dc.date.accessioned | 2024-10-18T16:17:29Z | |
dc.date.available | 2024-10-18T16:17:29Z | |
dc.date.issued | 2021-10 | |
dc.identifier.citation | Advanced Synthesis and Catalysis 363 : 4761-4769 (2021) | es_ES |
dc.identifier.issn | 1615-4169 | |
dc.identifier.issn | 1615-4150 | |
dc.identifier.uri | http://hdl.handle.net/10810/70033 | |
dc.description.abstract | An ytterbium catalyzed formal [3+3] cycloaddition of cyclic enamines and α,β-unsaturated ketones catalyzed is reported. The reaction proceeds with a ‘head to tail’ regioselectivity through a conjugate addition of the enamine moiety followed by an amine-carbonyl condensation. In addition the use of chiral enamines provided a high degree of stereoselectivity, driven by a possible balance between steric and π-stacking effects. The resulting bicyclic 1,4-dihydropyridines were evaluated as antiproliferative agents against A549 (carcinomic human alveolar basal epithelial cell) and SKOV3 (human ovarian carcinoma) human tumor cell lines. Good toxicities were found for some of the compounds against A549 and SKOV3 cell lines, with best IC50 values of 0.89 μM for A549 and 6.69 μM for SKOV3, and a very good selectivity was observed towards MRC5 (non-malignant) cell lines. | es_ES |
dc.description.sponsorship | Ministerio de Economía, Industria y Competividad (MINECO, RTI2018-101818-B-I00) Gobierno Vasco (GV, IT 992–16) | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICIU/RTI2018-101818-B-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.subject | annulation | es_ES |
dc.subject | γ-lactams | es_ES |
dc.subject | homogeneous catalysis | es_ES |
dc.subject | stereoselective | es_ES |
dc.subject | antiproliferative activity | es_ES |
dc.title | Stereo- and Regioselective [3+3] Annulation Reaction Catalyzed by Ytterbium: Synthesis of Bicyclic 1,4-Dihydropyridines. | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. | es_ES |
dc.relation.publisherversion | https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202100785 | es_ES |
dc.identifier.doi | 10.1002/adsc.202100785 | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |
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This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.