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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postprinted_JACS2020.pdf (1.36 Mo)
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Computational_method_SI_.pdf (1.35 Mo)
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SI_JACS_revised.pdf (8.83 Mo)
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