dc.creator | Carmona, José A. | es |
dc.creator | Hornillos, Valentín | es |
dc.creator | Ramírez López, Pedro | es |
dc.creator | Ros Lao, Abel | es |
dc.creator | Iglesias Sigüenza, Francisco Javier | es |
dc.creator | Gómez-Bengoa, Enrique | es |
dc.creator | Fernández Fernández, Rosario Fátima | es |
dc.creator | Lassaletta Simón, José María | es |
dc.date.accessioned | 2019-02-01T10:59:25Z | |
dc.date.available | 2019-02-01T10:59:25Z | |
dc.date.issued | 2018 | |
dc.identifier.citation | Carmona, J.A., Hornillos, V., Ramírez López, P., Ros Lao, A., Iglesias Sigüenza, F.J., Gómez-Bengoa, E.,...,Lassaletta Simón, J.M. (2018). A Dynamic Kinetic Asymmetric Heck Reaction for the Simultaneous Generation of Central and Axial Chirality. Journal of the American Chemical Society, 140 (35), 11067-11075. | |
dc.identifier.issn | 1520-5126 | es |
dc.identifier.uri | https://hdl.handle.net/11441/82335 | |
dc.description.abstract | A highly diastereo- and enantioselective, scalable Pd-catalyzed dynamic kinetic asymmetric Heck reaction of heterobiaryl sulfonates with electron-rich olefins is described. The coupling of 2,3-dihydrofuran or N-boc protected 2,3-dihydropyrrole with a variety of quinoline, quinazoline, phthalazine, and picoline derivatives takes place with simultaneous installation of central and axial chirality, reaching excellent diastereo- and enantiomeric excesses when in situ formed [Pd0/DM-BINAP] was used as the catalyst, with loadings reduced down to 2 mol % in large scale reactions. The coupling of acyclic, electron-rich alkenes can also be performed using a [Pd0/Josiphos ligand] to obtain axially chiral heterobiaryl α-substituted alkenes in high yields and enantioselectivities. Products from Boc-protected 2,3-dihydropyrrole can be easily transformed into N,N ligands or appealing axially chiral, bifunctional proline-type organocatalysts. Computational studies suggest that a β-hydride elimination is the stereocontrolling step, in agreement with the observed stereochemical outcome of the reaction. | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación (Grants CTQ2016-76908-C2-1-P; CTQ2016-76908-C2-2-P; CTQ2016-78083-P; RYC-2013-12585) | es |
dc.description.sponsorship | European Commission (FEDER Programme) | es |
dc.description.sponsorship | Junta de Andalucía (Grant 2012/FQM 10787) | es |
dc.description.sponsorship | Universidad de Sevilla (Grant No. 1800511201) | es |
dc.description.sponsorship | European Union - Marie Skłodowska-Curie (COFUND—Grant Agreement nº 291780) | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | American Chemical Society | es |
dc.relation.ispartof | Journal of the American Chemical Society, 140 (35), 11067-11075. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.title | A Dynamic Kinetic Asymmetric Heck Reaction for the Simultaneous Generation of Central and Axial Chirality | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/acceptedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | CTQ2016-76908-C2-1-P | es |
dc.relation.projectID | CTQ2016-76908-C2-2-P | es |
dc.relation.projectID | CTQ2016-78083-P | es |
dc.relation.projectID | RYC-2013-12585 | es |
dc.relation.projectID | 2012/FQM 10787 | es |
dc.relation.projectID | 1800511201 | es |
dc.relation.projectID | 291780 | es |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jacs.8b05819 | es |
dc.identifier.doi | 10.1021/jacs.8b05819 | es |
idus.format.extent | 9 p. | es |
dc.journaltitle | Journal of the American Chemical Society | es |
dc.publication.volumen | 140 | es |
dc.publication.issue | 35 | es |
dc.publication.initialPage | 11067 | es |
dc.publication.endPage | 11075 | es |
dc.description.awardwinning | Premio Anual Publicación Científica Destacada de la US. Facultad de Química | |