A chiral oxazaborolidine combined with SnCl4 has been found to promote the dearomative spirocyclization of electron-rich benzyl allenyl ketones. The reaction outcome is sensitive to the nature of activating acid, which was rationalized using hard-soft acid-base (HSAB) theory. The spirocyclic product was obtained with up to 72% ee, which is the best result reported to date for these substrates. The formation of cross-conjugated or conjugated products is readily controlled by changing the oxygen-protecting groups.