Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols

Please use this identifier to cite or link to this item: http://hdl.handle.net/10045/2507
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dc.contributorDerivados de Aminoácidos y Péptidos en Síntesis Orgánicaen
dc.contributorProcesos Catalíticos en Síntesis Orgánica-
dc.contributor.authorGuillena, Gabriela-
dc.contributor.authorHita López, María del Carmen-
dc.contributor.authorNájera, Carmen-
dc.contributor.otherUniversidad de Alicante. Departamento de Química Orgánicaen
dc.date.accessioned2007-10-27T17:33:19Z-
dc.date.available2007-10-27T17:33:19Z-
dc.date.issued2006-04-03-
dc.identifier.citationGUILLENA TOWNLEY, Gabriela; HITA, María del Carmen; NÁJERA DOMINGO, Carmen. "Organocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols". Tetrahedron: Asymmetry. Vol. 17, Issue 7 (3 Apr. 2006). ISSN 0957-4166, pp. 1027-1031en
dc.identifier.issn0957-4166-
dc.identifier.urihttp://hdl.handle.net/10045/2507-
dc.description.abstractRecoverable BINAM-prolinamide derivatives, as well as L-proline, give results complementary to antibodies when used as organocatalysts for aldol eactions between aldehydes and α-alkoxyacetones driving regioselectively to anti/syn-1,2-diols. The formation of the iso-regioisomer is suppressed using α-hydroxyacetone in DMSO at rt, achieving the corresponding anti-1,2-diol with ee’s up to 85%. For α-alkoxyacetones (methoxy, benzyloxy, and tert-butyldimethylsilyloxy), the highest regio- and diastereoselectivity is achieved using α-methoxyacetone in DMF at 0 °C; the enantiomeric excess for the anti-1,2-isomer being up to 98%.en
dc.description.sponsorshipThis work was financially supported by the Dirección General de Investigación of the Ministerio de Educación y Ciencia of Spain (Grant BQU2001-0724-CO2-01 and CTQ2004-00808/BQU), the Generalitat Valenciana (Grant CTIOIB/2002/320, GRUPOS03/134, and GV05/157) and the University of Alicante.en
dc.languageengen
dc.publisherElsevieren
dc.subjectOrganocatalysisen
dc.subjectAldolen
dc.subjectEnantioselectiveen
dc.subjectAsymmetric synthesisen
dc.subjectAmino acidsen
dc.subjectProlineen
dc.subject.otherQuímica Orgánicaen
dc.titleOrganocatalyzed direct aldol condensation using L-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diolsen
dc.typeinfo:eu-repo/semantics/articleen
dc.peerreviewedsien
dc.identifier.doi10.1016/j.tetasy.2006.03.023-
dc.relation.publisherversionhttp://dx.doi.org/10.1016/j.tetasy.2006.03.023-
dc.rights.accessRightsinfo:eu-repo/semantics/restrictedAccess-
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