Access to Pyrrolidine Imino Sugars via Tin(II)-Mediated Aldol Reactions of Bislactim Ethers: Synthesis of 2,5-Dideoxy-2,5-Imino-D-Glucitol

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UDC.coleccionInvestigaciónes_ES
UDC.departamentoQuímicaes_ES
UDC.endPage3969es_ES
UDC.grupoInvSíntese Asimétricaes_ES
UDC.issue21es_ES
UDC.journalTitleOrganic & Biomolecular Chemistryes_ES
UDC.startPage3967es_ES
UDC.volume6es_ES
dc.contributor.authorBlanco, Olga
dc.contributor.authorPato Pérez, Cristina María
dc.contributor.authorRuiz, María
dc.contributor.authorOjea, Vicente
dc.date.accessioned2024-08-09T07:49:02Z
dc.date.available2024-08-09T07:49:02Z
dc.date.issued2008-09-05
dc.descriptionAuthor accepted manuscriptes_ES
dc.description.abstract[Abstract] 2,5-Dideoxy-2,5-imino-D-glucitol (DGDP) has been synthesized via the tin(II)-mediated anti-selective aldol reaction of bislactim ether 5 and a 3-O-silylated 2,4-ethylidene-D-erythrose derivative 6. In accordance with density functional theory calculations (at the B3LYP/cc-pVDZ-PP level), pericyclic transition structures with a boat-like conformation and a stabilizing hydrogen bond can account for the unexpected stereoselectivity.es_ES
dc.description.sponsorshipWe gratefully acknowledge Ministerio de Ciencia y Tecnología (BQU2003-00692) and Xunta de Galicia (PGIDIT05BTF10301PR) for financial support. The authors are indebted to Centro de Supercomputación de Galicia for providing computer facilities. O. B. thanks Xunta de Galicia for an “Isidro Parga Pondal” position at Universidade da Coruñaes_ES
dc.description.sponsorshipXunta de Galicia; PGIDIT05BTF10301PRes_ES
dc.identifier.citationO. Blanco, C. Pato, M. Ruiz and V. Ojea, Access to pyrrolidine imino sugarsvia tin(II)-mediated aldol reactions of bislactim ethers: synthesis of 2,5-dideoxy-2,5-imino-D-glucitol, Org. Biomol. Chem., 2008, 6, 3967–3969.es_ES
dc.identifier.doi10.1039/B810878A
dc.identifier.issn1477-0539
dc.identifier.urihttp://hdl.handle.net/2183/38499
dc.language.isoenges_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICYT/Plan Nacional de I+D+i 2000-2003/BQU2003-00692/ES/es_ES
dc.relation.urihttps://doi.org/10.1039/B810878Aes_ES
dc.rights.accessRightsopen accesses_ES
dc.titleAccess to Pyrrolidine Imino Sugars via Tin(II)-Mediated Aldol Reactions of Bislactim Ethers: Synthesis of 2,5-Dideoxy-2,5-Imino-D-Glucitoles_ES
dc.typejournal articlees_ES
dspace.entity.typePublication
relation.isAuthorOfPublication1b62ed73-b69c-46e0-83a5-46537ebbbf12
relation.isAuthorOfPublication51cb91d3-79ab-444d-a358-e798775f3f54
relation.isAuthorOfPublication5cf715bc-5c4a-440d-a9be-a0d501b76a1b
relation.isAuthorOfPublication.latestForDiscovery1b62ed73-b69c-46e0-83a5-46537ebbbf12

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