dc.creator | Carmona, José A. | es |
dc.creator | Gonzalo Calvo, Gonzalo de | es |
dc.creator | Serrano Vallez, Inmaculada | es |
dc.creator | Crespo-Peña, Ana | es |
dc.creator | Šimek, Michal | es |
dc.creator | Monge Fernández, David | es |
dc.creator | Fernández, Rafael | es |
dc.creator | Lassaletta, José M. | es |
dc.date.accessioned | 2018-05-24T17:41:52Z | |
dc.date.available | 2018-05-24T17:41:52Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | Carmona, J.A., Gonzalo Calvo, G., Murcia Serrano, I., Crespo-Peña, A., Šimek, M., Monge, D.,...,Lassaletta, J.M. (2017). Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters. Organic and Biomolecular Chemistry, 15, 2993-3005. | |
dc.identifier.issn | 1477-0520 | es |
dc.identifier.uri | https://hdl.handle.net/11441/75103 | |
dc.description.abstract | A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters for the synthesis of tertiary azomethyl alcohols. Using the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-d-glucosamine derived 3,5-bis-(trifluoromethyl)phenyl thiourea the reaction could be accomplished with high yields (75-98%) and moderate enantioselectivities (50-64% ee). Subsequent high-yielding and racemization-free tranformations of both aromatic- and aliphatic-substituted diazene products in a one pot fashion provide a direct entry to valuable azoxy compounds and α-hydroxy-β-amino esters. | es |
dc.description.sponsorship | Ministerio de Economía y Competitividad CTQ2016-76908-C2-1-P, CTQ2016- 76908-C2-2-P, contract RYC-2012-10014 for G. de G. | es |
dc.description.sponsorship | European Funds FEDER | es |
dc.description.sponsorship | Junta de Andalucía 2012/FQM 1078 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | Royal Society of Chemistry (Great Britain) | es |
dc.relation.ispartof | Organic and Biomolecular Chemistry, 15, 2993-3005. | |
dc.rights | Atribución-NoComercial-SinDerivadas 3.0 Estados Unidos de América | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.title | Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters | 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.publisherversion | http://dx.doi.org/10.1039/c7ob00308k | es |
dc.identifier.doi | 10.1039/c7ob00308k | es |
idus.format.extent | 12 | es |
dc.journaltitle | Organic and Biomolecular Chemistry | es |
dc.publication.issue | 15 | es |
dc.publication.initialPage | 2993 | es |
dc.publication.endPage | 3005 | es |