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Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis

dc.creatorHerrera González, Irenees
dc.creatorSánchez Fernández, Elena Matildees
dc.creatorSau, Abhijites
dc.creatorNativi, Cristinaes
dc.creatorGarciá Fernández, José M.es
dc.creatorGalán, M. Carmenes
dc.creatorOrtiz Mellet, Carmenes
dc.date.accessioned2022-11-30T15:36:52Z
dc.date.available2022-11-30T15:36:52Z
dc.date.issued2020
dc.identifier.citationHerrera González, I., Sánchez Fernández, E.M., Sau, A., Nativi, C., Garciá Fernández, J.M., Galán, M.C. y Ortiz Mellet, C. (2020). Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis. Journal of Organic Chemistry, 85 (7), 5038-5047. https://doi.org/10.1021/acs.joc.0c00324.
dc.identifier.issn0022-3263es
dc.identifier.issn1520-6904es
dc.identifier.urihttps://hdl.handle.net/11441/139948
dc.description.abstractThe first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium nitrate efficiently promoted the formation of 2-deoxy S-glycosides in the presence of thiols, probably by in situ generation of catalytic HNO3, with complete α-stereoselectivity. Cooperative phosphoric acid/Schreiner's thiourea organocatalysis proved better suited for generating 2-deoxy O-glycosides, significantly broadening the scope of the approach.es
dc.description.sponsorshipMinisterio de Economía y Competitividad SAF201676083-Res
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades RTI2018-097609-B-C21es
dc.description.sponsorshipEuropean Cooperation in Science and Technology CA18132es
dc.description.sponsorshipConsejo Europeo de Investigación ERC-COG: 648239es
dc.formatapplication/pdfes
dc.format.extent12 p.es
dc.language.isoenges
dc.publisherAmerican Chemical Societyes
dc.relation.ispartofJournal of Organic Chemistry, 85 (7), 5038-5047.
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subject2-deoxyglycosideses
dc.subjectIminosugarses
dc.subjectCerium ammonium nitratees
dc.subjectOrganocatalysises
dc.subjectIminoglycales
dc.titleStereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysises
dc.typeinfo:eu-repo/semantics/articlees
dcterms.identifierhttps://ror.org/03yxnpp24
dc.type.versioninfo:eu-repo/semantics/acceptedVersiones
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.contributor.affiliationUniversidad de Sevilla. Departamento de Química orgánicaes
dc.relation.projectIDSAF201676083-Res
dc.relation.projectIDRTI2018-097609-B-C21es
dc.relation.projectIDCA18132es
dc.relation.projectIDERC-COG: 648239es
dc.relation.publisherversionhttps://dx.doi.org/10.1021/acs.joc.0c00324es
dc.identifier.doi10.1021/acs.joc.0c00324es
dc.journaltitleJournal of Organic Chemistryes
dc.publication.volumen85es
dc.publication.issue7es
dc.publication.initialPage5038es
dc.publication.endPage5047es
dc.contributor.funderMinisterio de Economía y Competitividad (MINECO). Españaes
dc.contributor.funderMinisterio de Ciencia, Innovación y Universidades (MICINN). Españaes
dc.contributor.funderEuropean Cooperation in Science and Technology (COST)es
dc.contributor.funderConsejo Europeo de Investigaciónes

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