Asymmetric halolactonizations are powerful methods for the syntheses of chiral lactones. Catalytic and highly enantioselective halolactonizations of α-allyl carboxylic acids, however, continue to present a formidable challenge. Herein, we report the chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonizations of α,α-diallyl carboxylic acids. These reactions efficiently produced chiral α-quaternary lactones and esters.