2026-06-29T16:48:25Zhttps://docta.ucm.es/rest/oai/requestoai:docta.ucm.es:20.500.14352/1089972025-07-17T16:45:03Zcom_20.500.14352_14col_20.500.14352_15
Enantioselective synthesis of a-aryl a-hydrazino phosphonates
Alberca, Saúl
Romero Parra, Javier
Fernández López, Israel
Fernández, Rosario
Lassaletta, José M.
Monge, David
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.
2024-10-16T07:44:16Z
2024-10-16T07:44:16Z
2024
journal article
10.1039/d4sc00822g
https://hdl.handle.net/20.500.14352/108997
https://doi.org/10.1039/D4SC00822G
https://pubs.rsc.org/en/content/articlelanding/2024/sc/d4sc00822g
eng
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C21/ES/CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVA/
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106358GB-C22/ES/CATALIZADORES, LIGANDOS, METODOS Y REACTIVOS PARA SINTESIS ORGANICA SELECTIVA/
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106184GB-I00/ES/UNA APROXIMACION DIFERENTE PARA ENTENDER Y CONTROLAR LA CATALISIS/
PID2022-137888NB-I00
PID2022-143230NB-I00
PID2022-139318NB-I00
RED2022-134287-T
P18-FR-3531
P18-FR-644
US-1262867
http://creativecommons.org/licenses/by-nc-nd/4.0/
open access
Attribution-NonCommercial-NoDerivatives 4.0 International
RSC