The enantioselective bromocyclization of allenes is accomplished through the use of a chiral dinuclear gold complex and/or chiral phosphate anions in the presence of an N-bromolactam as an electrophilic bromine source. This method provides access to heterocyclic vinyl bromides with an allylic stereocenter in excellent yield and enantioselectivity. These enantioenriched vinyl bromides may serve as a handle for further derivatization via cross-coupling reactions. © 2013 The Royal Society of Chemistry.