Artículos (Química Orgánica)

URI permanente para esta colecciónhttps://hdl.handle.net/11441/10924

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Examinando Artículos (Química Orgánica) por Autor "Alberca, Saúl"

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    Enantioselective synthesis of α-aryl α-hydrazino phosphonates
    (Royal Society of Chemistry, 2024-05-23) Alberca, Saúl; Romero-Parra, Javier; Fernández López, Israel; Fernández Fernández, Rosario Fátima; Lassaletta, José M.; Monge Fernández, David; Universidad de Sevilla. Departamento de Química orgánica; Ministerio de Ciencia, Innovación y Universidades (MICINN). España; Junta de Andalucía
    Catalysts generated in situ by the combination of pyridine-hydrazone N,N-ligands and Pd(TFA)2 have been applied to the addition of arylboronic acids to formylphosphonate-derived hydrazones, yielding α-aryl α-hydrazino phosphonates in excellent enantioselectivities (96 → 99% ee). Subsequent removal of the benzyloxycarbonyl (Cbz) N-protecting group afforded key building blocks en route to appealing artificial peptides, herbicides and antitumoral derivatives. Experimental and computational data support a stereochemical model based on aryl-palladium intermediates in which the phosphono hydrazone coordinates in its Z-configuration, maximizing the interactions between the substrate and the pyridine-hydrazone ligand.