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dc.contributor.authorSedano Labrador, Carlos 
dc.contributor.authorVelasco, Rocío
dc.contributor.authorSuárez Pantiga, Samuel 
dc.contributor.authorSanz Díez, Roberto 
dc.date.accessioned2020-10-29T11:32:16Z
dc.date.available2020-10-29T11:32:16Z
dc.date.issued2020-10
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10259/5535
dc.description.abstractα-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot manner. These products are obtained as single diastereoisomers bearing a quaternary stereocenter. The complete diastereocontrol of the aldol-Tishchenko process is attributed to stereoelectronic preferences in the transition state.es
dc.description.sponsorshipMinisterio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P) and Junta de Castilla y León and FEDER (BU291P18)es
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherAmerican Chemical Societyes
dc.relation.ispartofOrganic Letters. 2020, V. 22, n. 20, p. 8070–8075es
dc.subjectReaction productses
dc.subjectAldehydeses
dc.subjectEtherses
dc.subjectPharmaceuticalses
dc.subjectAldol reactionses
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleMerging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Etherses
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.0c03014es
dc.identifier.doi10.1021/acs.orglett.0c03014
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN/CTQ2016-75023-C2-1-P
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU291P18
dc.identifier.essn1523-7052
dc.journal.titleOrganic Letterses
dc.volume.number22es
dc.issue.number20es
dc.page.initial8070es
dc.page.final8075es
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersiones


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