Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2020

Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis

Résumé

Tethering a metal complex to its phosphate counterion via a phosphine ligand enables a new strategy in Asymmetric Counteranion-Directed Catalysis (ACDC). A straightforward, scalable synthetic route gives access to the gold(I) complex of a chiral phosphine displaying a phos-phoric acid function. The complex generates a catalytically active species with an unprecedented intramolecular relationship between the cati-onic Au(I) center and the phosphate counterion. The benefits of tethering the two functions of the catalyst is demonstrated here in a tandem cycloisomerization/nucleophilic addition reaction, by attaining high enantioselectivity levels (up to 97% ee) at a remarkable low 0.2 mol% catalyst loading. Remarkably the method is also compatible with a silver-free protocol.
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Dates et versions

hal-02471058 , version 1 (07-02-2020)

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Zhenhao Zhang, Vitalii Smal, Pascal Retailleau, Arnaud Voituriez, Gilles Frison, et al.. Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis. Journal of the American Chemical Society, 2020, 142, pp.3797-3805. ⟨10.1021/jacs.9b11154⟩. ⟨hal-02471058⟩
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