ArticleEuropean journal of organic chemistry2022
H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study.
Article in European journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed, 21 citations in OpenAlex.
- Chiral Hydrogen-Bond Donor and Gold(I) Cocatalysis Enables Enantioselective Dearomative Spirocyclization of Naphthols.Journal of the American Chemical Society · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Practical Synthesis of Chiral Ferrocenenylphosphino-Gold(I) Catalysts and NEST Analysis of the Enantioinduction.ACS catalysis · 2025Article
- A Ligand-Controlled Approach Enabling Gold(I)-Catalyzed Stereoinvertive Glycosylation with Primal GlycosylJournal of the American Chemical Society · 2024Article
- On the gold(I)-catalyzed enantioselective addition of indole to diphenylallene via anion-binding catalysis.Tetrahedron letters · 2024Article
- A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-Beilstein journal of organic chemistry · 2024Article
- Hydrogen-Bonded Matched Ion Pair Gold(I) Catalysis.ACS catalysis · 2023Article
- H-Bonded Counterion-Directed Catalysis: Enantioselective Gold(I)-Catalyzed Addition to 2-Alkynyl Enones as a Case Study.European journal of organic chemistry · 2022Article
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4 authors at 1 institution in 1 country.
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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 Δee% was observed upon addition of the achiral Au(I) component to the Ag(I) salt.
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