Author, as appears in the article.: Marti, Alex; Montesinos-Magraner, Marc; Echavarren, Antonio M.; Franchino, Allegra;

Department: Química Analítica i Química Orgànica

URV's Author/s: ECHAVARREN PABLOS, ANTONIO

Keywords: 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

Abstract: 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.

Thematic Areas: 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

licence for use: https://creativecommons.org/licenses/by/3.0/es/

Author's mail: antoniomaria.echavarren@urv.cat

Author identifier: 0000-0002-6418-7930

Record's date: 2023-05-14

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202200518

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: European Journal Of Organic Chemistry. 2022 (38):

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

Article's DOI: 10.1002/ejoc.202200518

Entity: Universitat Rovira i Virgili

Journal publication year: 2022

Publication Type: Journal Publications