dc.creator | Arribas Nieto, Inmaculada | es |
dc.creator | Rubio Moreno, Miguel | es |
dc.creator | Kleman, Patryk Artur | es |
dc.creator | Pizzano Mancera, Antonio | es |
dc.date.accessioned | 2018-02-15T15:39:15Z | |
dc.date.available | 2018-02-15T15:39:15Z | |
dc.date.issued | 2013 | |
dc.identifier.citation | Arribas Nieto, I., Rubio Moreno, M., Kleman, P.A. y Pizzano Mancera, A. (2013). Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives. Journal of Organic Chemistry, 78, 3997-4005. | |
dc.identifier.issn | 0022-3263 (impreso) | es |
dc.identifier.issn | 1520-6904 (electrónico) | es |
dc.identifier.uri | https://hdl.handle.net/11441/70327 | |
dc.description.abstract | The enantioselective catalytic hydrogenation of N-(3,4-dihydronaphthalen-2- yl) amides (1) with rhodium catalysts bearing phosphine-phosphite ligands 4 has been studied. A wide catalyst screening, facilitated by the modular structure of 4, has found a highly enantioselective catalyst for this reaction. This catalyst gives a 93% ee in the hydrogenation of 1a and also produces high enantioselectivities, ranging from 83 to 93% ee, in the hydrogenation of several OMe- and Br-substituted substrates. In contrast, the structurally related enol esters 2 are very reluctant to undergo hydrogenation. A coordination study of the representative enamide 1d has shown an unusual η6-arene coordination mode, over the typical O,C,C chelating mode for enamides, as the preferred one for this substrate in a Rh(I) complex. Deuteration reactions of 1c,d indicate a clean syn addition of deuterium to the double bond without an isotopic effect on the enantioselectivity. | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación CTQ2009-11867, CSD2007-00006 | es |
dc.description.sponsorship | Junta de Andalucía 2008/FQM-3830, 2009/FQM-4832 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | American Chemical Society | es |
dc.relation.ispartof | Journal of Organic Chemistry, 78, 3997-4005. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.title | Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/submittedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.relation.projectID | CTQ2009-11867 | es |
dc.relation.projectID | CSD2007-00006 | es |
dc.relation.projectID | 2008/FQM-3830 | es |
dc.relation.projectID | 2009/FQM-4832 | es |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo400345v | es |
dc.identifier.doi | 10.1021/jo400345v | es |
idus.format.extent | 29 p. | es |
dc.journaltitle | Journal of Organic Chemistry | es |
dc.publication.volumen | 78 | es |
dc.publication.initialPage | 3997 | es |
dc.publication.endPage | 4005 | es |
dc.contributor.funder | Ministerio de Ciencia e Innovación (MICIN). España | |
dc.contributor.funder | Junta de Andalucía | |