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An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using N -iodosuccinimide as a promoter, simultaneously constructing one new C-O bond and two new C-C bonds. A tetra-substituted vinylidene ortho -quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.

An organocatalyzed enantioselective γ-elimination process has been achieved and applied in the kinetic resolution of peroxides to access chiral peroxides and epoxides. The reaction provided a pathway for the preparation of two useful synthetic and biologically important structural motifs through a single-step reaction. A range of substrates has been resolved with a selectivity factor up to 63. The obtained enantioenriched peroxides and epoxides allowed a series of transformations with retained optical purities.