Ag/Brønsted Acid Co-Catalyzed Spiroketalization of β‑Alkynyl Ketones toward Spiro[chromane-2,1′-isochromene] Derivatives

A new Ag/Brønsted acid co-catalyzed spiroketalization of β-alkynyl ketones with para-quinone methides (p-QMs) has been established, enabling multiple C–C and C–O bond-forming events to access densely functionalized spiro­[chromane-2,1′-isochromene] derivatives with generally excellent diastereoselectivity and good yields. A reasonable mechanism for forming these 6,6-dibenzannulated spiroketals involving 6-endo-dig oxo-cyclization and 1,6-addition-cyclization cascades is proposed.