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dc.contributor.authorSedano Labrador, Carlos
dc.contributor.authorVirumbrales, Cintia 
dc.contributor.authorSuarez Pantiga, Samuel 
dc.contributor.authorSanz Díez, Roberto 
dc.date.accessioned2021-11-04T09:23:20Z
dc.date.available2021-11-04T09:23:20Z
dc.date.issued2021-10
dc.identifier.issn0039-7881
dc.identifier.urihttp://hdl.handle.net/10259/6089
dc.description.abstractα-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes.en
dc.description.sponsorshipMinisterio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P), and Junta de Castilla y León and FEDER (BU291P18, BU049P20). The project leading to these results has also received funding from the “la Caixa” Foundation, under agreement LCF/PR/PR18/51130007) (CAIXA-UBU001). A postdoctoral contract (S.S.-P.) and a predoctoral contract (C.S.) were funded by Junta de Castilla y León and FEDER and Ministerio de Educación (FPU), respectivelyen
dc.format.mimetypeapplication/pdf
dc.language.isoengen
dc.publisherThieme
dc.relation.ispartofSynthesis. 2021, V. 53, n. 20, p. 3725-3734en
dc.subjectaldol–Tishchenko reactionen
dc.subjectenolatesen
dc.subjectα-oxy ketonesen
dc.subjectpolyol derivativesen
dc.subjectdiastereoselectivityen
dc.subjectoxetanesen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleAldol–Tishchenko Reaction of α-Oxy Ketones: Diastereoselective Synthesis of 1,2,3-Triol Derivativesen
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.accessRightsinfo:eu-repo/semantics/embargoedAccesses
dc.relation.publisherversionhttps://doi.org/10.1055/a-1509-5655
dc.identifier.doi10.1055/a-1509-5655
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersiones


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