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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Espinosa López, Miguel; Blay Llinares, Gonzalo Perfil; Cardona Prósper, María Luz; Merino, Pedro; Pedro, José Ramón
This document is a artículoDate2019
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.

    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
https://doi.org/10.1039/C9QO00741E

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