Chiral Hydrogen-Bond Donor and Gold(I) Cocatalysis Enables Enantioselective Dearomative Spirocyclization of Naphthols.

ABSTRACT: 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 with 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 the gold(I) phosphine ligand and the observed enantioselectivity.

SUBMITTER: Adrianov T 

PROVIDER: S-EPMC12860481 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature