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Updated: Jun 25, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Enantioselective synthesis of α-aryl α-hydrazino phosphonates
Saúl Alberca1, Javier Romero-Parra2, Israel Fernández3
1Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO-CINQA) C/ Prof. García González, 1 41012 Sevilla Spain ffernan@us.es dmonge@us.es.
Abstract:
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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