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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.citation	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.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.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	journal article	es_ES
dc.date.updated	2020-09-29T16:45:47Z
dc.identifier.doi	10.1039/C9QO00741E
dc.identifier.idgrec	134311
dc.rights.accessRights	open access	es_ES