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dc.contributor.authorEscorihuela Fuentes, Jorge
dc.contributor.authorAltava Benito, Belén
dc.contributor.authorBurguete Azcárate, María Isabel
dc.contributor.authorLuis Lafuente, Santiago Vicente
dc.date.accessioned2014-05-05T09:51:46Z
dc.date.available2014-05-05T09:51:46Z
dc.date.issued2013-01
dc.identifier.urihttp://hdl.handle.net/10234/91312
dc.description.abstractA series of C2 symmetrical 1:2 Ni:L complexes derived from α-amino amides were studied for the enantioselective addition of dialkylzinc reagents to aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Through optimization of structure and reaction conditions, the best ligand provided secondary alcohols in excellent yields (up to 98%) and enantioselectivity of up to 99% ee for (R)-enantiomer. A transition state model has been proposed to explain the observed enantioselectivities based on computational calculations at the DFT level. Very interestingly, calculations suggest a coordination model of the aldehyde to the metal complex through association of a lone pair of the carbonyl oxygen to the hydrogen atom of an amino group.ca_CA
dc.format.extent7 p.ca_CA
dc.format.mimetypeapplication/pdfca_CA
dc.language.isoengca_CA
dc.publisherElsevierca_CA
dc.relation.isPartOfTetrahedron Volume 69, Issue 2, 14 January 2013ca_CA
dc.subjectAsymmetric catalysisca_CA
dc.subjectOrganozincca_CA
dc.subjectAmino amideca_CA
dc.subjectEnantioselectivityca_CA
dc.subjectAldehydeca_CA
dc.titleC2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydesca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1016/j.tet.2012.11.025
dc.rights.accessRightsinfo:eu-repo/semantics/restrictedAccessca_CA
dc.relation.publisherVersionhttp://www.sciencedirect.com/science/article/pii/S0040402012017188ca_CA


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