%0 Journal Article
%A Alberca, Saúl
%A Romero Parra, Javier
%A Fernández López, Israel
%A Fernández, Rosario
%A Lassaletta, José M.
%A Monge, David
%T Enantioselective synthesis of a-aryl a-hydrazino phosphonates
%D 2024
%U https://hdl.handle.net/20.500.14352/108997
%X 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.
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