Autor segons l'article: Marti, Alex; Montesinos-Magraner, Marc; Echavarren, Antonio M.; Franchino, Allegra;
Departament: Química Analítica i Química Orgànica
Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO / Martí Zaragoza, Àlex / Montesinos Magraner, Marc
Paraules clau: Ynenones Transfer hydrogenation Platinum Ligands Hydrogen bonding Highly substituted furans Gold complexes Gold Cycloisomerization Cycloaddition Cyclization Chiral counterion Chiral anions Asymmetric catalysis 2-(1-alkynyl)-2-alken-1-ones
Resum: H-bonded counterion-directed catalysis (HCDC) is a strategy wherein a chiral anion that is hydrogen-bonded to the achiral ligand of a metal complex is responsible for enantioinduction. In this article we present the application of H-bonded counterion-directed catalysis to the Au(I)-catalyzed enantioselective tandem cycloisomerization-addition reaction of 2-alkynyl enones. Following the addition of C-, N- or O-centered nucleophiles, bicyclic furans were obtained in moderate to excellent yield and enantioselectivity (28 examples, 59-96 % yield, 62 : 38 to 95 : 5 er). The optimal catalytic system, comprising a phosphinosquaramide Au(I) chloride complex and a BINOL-derived phosphoramidate Ag(I) salt, was selected in a combinatorial fashion from a larger library with the help of high-throughput screening. An enantioselectivity switch of ca. 120 Delta ee% was observed upon addition of the achiral Au(I) component to the Ag(I) salt.
Àrees temàtiques: Química Physical and theoretical chemistry Organic chemistry Materiais Interdisciplinar Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Biodiversidade Astronomia / física
Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat alex.marti@estudiants.urv.cat
Identificador de l'autor: 0000-0002-6418-7930
Data d'alta del registre: 2024-09-07
Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
Referència a l'article segons font original: European Journal Of Organic Chemistry. 2022 (38):
Referència de l'ítem segons les normes APA: Marti, Alex; Montesinos-Magraner, Marc; Echavarren, Antonio M.; Franchino, Allegra; (2022). H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study. European Journal Of Organic Chemistry, 2022(38), -. DOI: 10.1002/ejoc.202200518
Entitat: Universitat Rovira i Virgili
Any de publicació de la revista: 2022
Tipus de publicació: Journal Publications
Repositori URV