Regioselectivity switch based on the stoichiometry: stereoselective synthesis of trisubstituted vinyl epoxides by Cu-catalyzed 3-exo-trig cyclization of α-allenols
| dc.contributor.author | Luna Costales, Amparo | |
| dc.contributor.author | Esteban Arderíus, Pablo | |
| dc.contributor.author | Herrera García, Fernando | |
| dc.contributor.author | San Martín Loubet, Daniel | |
| dc.contributor.author | Almendros Requena, Pedro | |
| dc.date.accessioned | 2025-01-17T11:18:36Z | |
| dc.date.available | 2025-01-17T11:18:36Z | |
| dc.date.issued | 2022-08-10 | |
| dc.description.abstract | Typical transition metal-catalyzed oxycyclization of allenols takes place at the terminal allene carbon via a 5-endo path and forms dihydrofurans. A copper-catalyzed protocol brought about a reversed regioselectivity, generating a series of trisubstituted epoxides through a 3-exo-cyclization/sulfonylation cascade. The current stoichiometry control of regioselectivity may open singular opportunities in chemical transformations. | |
| dc.description.department | Depto. de Química Orgánica | |
| dc.description.faculty | Fac. de Ciencias Químicas | |
| dc.description.refereed | TRUE | |
| dc.description.sponsorship | Ministerio de Ciencia e Innovación (España) | |
| dc.description.sponsorship | Agencia Estatal de Investigación (España) | |
| dc.description.sponsorship | European Commission | |
| dc.description.status | pub | |
| dc.identifier.citation | Esteban P, Herrera F, San Martín D, Luna A, Almendros P. Regioselectivity Switch Based on the Stoichiometry: Stereoselective Synthesis of Trisubstituted Vinyl Epoxides by Cu‐Catalyzed 3‐exo‐trig Cyclization of α‐Allenols. Advanced Synthesis & Catalysis. 2022, 364, 3289–3294. | |
| dc.identifier.doi | 10.1002/adsc.202200592 | |
| dc.identifier.essn | 1615-4169 | |
| dc.identifier.issn | ISSN:1615-4150 | |
| dc.identifier.officialurl | https://doi.org/10.1002/adsc.202200592 | |
| dc.identifier.relatedurl | https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200592 | |
| dc.identifier.relatedurl | https://digital.csic.es/handle/10261/289436 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.14352/114881 | |
| dc.issue.number | 18 | |
| dc.journal.title | Advanced Synthesis and Catalysis | |
| dc.language.iso | eng | |
| dc.page.final | 3294 | |
| dc.page.initial | 3289 | |
| dc.publisher | Wiley-VCH | |
| dc.relation.projectID | MCIN/AEI /10.13039/501100011033 | |
| dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-095025-B-I00/ES/NUEVAS ESTRATEGIAS SINTETICAS DE CICLACION Y REAGRUPAMIENTO BASADAS EN ALENOS Y ALQUINOS PARA LA SINTESIS EFICIENTE DE MOLECULAS ORGANICAS DE INTERES/ | |
| dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 International | en |
| dc.rights.accessRights | open access | |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | |
| dc.subject.cdu | 547 | |
| dc.subject.keyword | Allenes | |
| dc.subject.keyword | Copper | |
| dc.subject.keyword | Cyclization | |
| dc.subject.keyword | Regioselectivity | |
| dc.subject.keyword | Sulfones | |
| dc.subject.ucm | Química orgánica (Química) | |
| dc.subject.unesco | 2306 Química Orgánica | |
| dc.subject.unesco | 2306.14 Química de Los Organosulfurados | |
| dc.title | Regioselectivity switch based on the stoichiometry: stereoselective synthesis of trisubstituted vinyl epoxides by Cu-catalyzed 3-exo-trig cyclization of α-allenols | |
| dc.type | journal article | |
| dc.type.hasVersion | AM | |
| dc.volume.number | 364 | |
| dspace.entity.type | Publication | |
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| relation.isAuthorOfPublication | ee8363b4-4019-453d-abd3-6258ecc4299f | |
| relation.isAuthorOfPublication.latestForDiscovery | 14581fe9-97b8-4d33-920f-23f4778c49f7 |
