We report a palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones with alkenyl-[2-(hydroxymethyl)phenyl]dimethylsilanes, providing 1-indanones bearing a versatile alkenyl group and an all-carbon quaternary center. Our methodology was utilized as the key step in the asymmetric total synthesis of (+)-herbertene-1,14-diol.