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Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide

dc.contributor.authorVera Salas, Silvia
dc.contributor.authorVázquez, Ana
dc.contributor.authorRodríguez Urretavizcaya, Ricardo
dc.contributor.authorDel Pozo, Sandra
dc.contributor.authorUrruzuno Guiu, Iñaki
dc.contributor.authorDe Cózar Ruano, Abel
dc.contributor.authorMielgo Vicente, María Antonia ORCID
dc.contributor.authorPalomo Nicolau, Claudio
dc.date.accessioned2024-02-01T16:12:21Z
dc.date.available2024-02-01T16:12:21Z
dc.date.issued2021-05-16
dc.identifier.citationJournal of Organic Chemistry 86(11) : 7757-7772 (2021)es_ES
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10810/64557
dc.description.abstractHere we report the highly enantio- and syn-selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Brønsted base (BB) catalysis. The key of this approach is the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.es_ES
dc.description.sponsorshipSupport has been provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22), Basque Government (GV grant IT1236-19), and Ministerio de Ciencia e Innovación (MICINN, CTQ2016-78487-C2), Spain. A.V. thanks Basque Government, and I.U. and S.d.P. thank UPV/EHU. We also thank SGIker (UPV/EHU) for providing NMR, HRMS, X-ray, and computational resources.es_ES
dc.language.isoenges_ES
dc.publisherACSes_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/CTQ2016-78487-C2es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleSynthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilidees_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2021 American Chemical Society. This publication is licensed under CC-BY 4.0.es_ES
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.1c00406es_ES
dc.identifier.doi10.1021/acs.joc.1c00406
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES


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© 2021 American Chemical Society. This publication is licensed under CC-BY 4.0.
Except where otherwise noted, this item's license is described as © 2021 American Chemical Society. This publication is licensed under CC-BY 4.0.