New chiral ligand containing butyl and dibutylmagnesiates have been prepared from a range of ligands and their reactivity studied. The reagents were generally efficient in promoting the clean bromine-magnesium exchange of 2-bromopyridine at room temperature and the subsequent reaction with aldehydes to afford α-substituted 2-pyridylcarbinols in good yields. (R,R)-TADDOLate proved to be the best ligand, leading to acceptable to good enantioselectivities. To the best of our knowledge this is the first example of an organomagnesiate-induced halogen-metal exchange followed by an enantioselective addition.