2026-04-05T10:52:09Zhttps://recercat.cat/oai/request

oai:recercat.cat:2072/5227262024-12-20T20:40:58Zcom_2072_300912com_2072_4427col_2072_301309

H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study Martí, Àlex Montesinos-Magraner, Marc Echavarren, Antonio M. Franchino, Allegra 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 Δee% was observed upon addition of the achiral Au(I) component to the Ag(I) salt. 2022-09-29T14:47:03Z 2024-04-23T10:57:55Z 2022-09-29T14:47:03Z 2024-04-23T10:57:55Z 2022-06-23 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://hdl.handle.net/2072/522726 https://doi.org/10.1002/ejoc.202200518 eng Horizon 2020 Marie Skłodowska- Curie COFUND fellowship 754510 to A.F. Advanced Grant 835080 MCIN/AEI/10.13039/ 501100011033 (PID2019-104815GB- I00) MCIN/AEI/10.13039/ 501100011033 (IJC2019040181-I Juan de la Cierva contract to M.M.-M.) Severo Ochoa Excellence Accreditation 2020–2023 (CEX2019-000925-S, MIC/AEI) info:eu-repo/semantics/openAccess You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License. This license is permanently located at http://creativecommons.org/licenses/by-nc-nd/4.0/. RECERCAT (Dipòsit de la Recerca de Catalunya)