Asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to conjugated imines enabled by catalyst metal change
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Asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to conjugated imines enabled by catalyst metal change

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Asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to conjugated imines enabled by catalyst metal change

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dc.contributor.author Espinosa López, Miguel
dc.contributor.author Blay Llinares, Gonzalo
dc.contributor.author Cardona Prósper, María Luz
dc.contributor.author Merino, Pedro
dc.contributor.author Pedro, José Ramón
dc.date.accessioned 2020-09-29T16:45:46Z
dc.date.available 2020-09-29T16:45:46Z
dc.date.issued 2019
dc.identifier.uri https://hdl.handle.net/10550/75690
dc.description.abstract Despite recent progress in asymmetric diastereodivergent reactions leading to products bearing two stereogenic centers, little research has been devoted to processes were a stereogenic center and a double bond are formed. Here, we report the asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to N-tosyl β,γ-unsaturated α-ketimino esters to give chiral α,β-dehydro-α-aminoesters bearing either a Z or E enamine moiety, using pyBOX-metal complexes. Diastereodivergency is achieved by simply changing the metal ion from a trivalent La(III) to a divalent Ca(II) ion, providing the Z or E enamines. Computational studies reveal the crucial role of London interactions between the aromatic residues on the imine and the pyBOX ligand, which are conditioned by the different coordination modes of La(III) and Ca(II), in the change of selectivity depending on the used metal.
dc.language.iso eng
dc.relation.ispartof Organic Chemistry Frontiers, 2019, vol. 6, p. 2907-2915
dc.rights.uri info:eu-repo/semantics/openAccess
dc.source Espinosa López, Miguel Blay Llinares, Gonzalo Cardona Prósper, María Luz Merino, Pedro Pedro, José Ramón 2019 Asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to conjugated imines enabled by catalyst metal change Organic Chemistry Frontiers 6 2907 2915
dc.subject Química orgànica
dc.subject Catàlisi
dc.title Asymmetric diastereodivergent Michael addition of 2-chloromalonate esters to conjugated imines enabled by catalyst metal change
dc.type info:eu-repo/semantics/article
dc.date.updated 2020-09-29T16:45:47Z
dc.identifier.doi https://doi.org/10.1039/C9QO00741E
dc.identifier.idgrec 134311

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