Gold (III) Chloride-Catalyzed 6-- Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Alkynones were treated with boron trifluoride diethyl etherate to generate β-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems.