Gold(I) catalysis achieves high enantioselectivity in spirocyclization of naphthols, suggesting promising applications.
We report the enantioselective gold(I)-catalyzed dearomative spirocyclization of naphthols enabled by the cooperative effect of chiral dual hydrogen-bond donors (HBDs). The reaction affords carbocyclic and heterocyclic spirocycles bearing a quaternary stereocenter in high enantioselectivity (up to 99% enantiomeric excess). Kinetic analysis supports a mode of catalysis wherein two molecules of a monomeric urea cocatalyst activate the neutral gold(I) sulfonate complex via anion abstraction to induce enantioselectivity and rate acceleration in the cyclization reaction. A systematic investigation of ligand effects identified a correlation between the electronic properties of gold(I) phosphine ligand and observed enantioselectivity.
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Adrianov et al. (2025) studied this question.
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