To introduce the (S)-configured methyl group, a versatile preparative strategy toward multisubstituted benzylamines with a stereochemically defined methyl group at the benzylic position was accomplished. We started from substituted 4-bromobenzoic acids 54, which were initially converted to 55 through Weinreb ketone synthesis applying methylmagnesium iodide, or directly from the corresponding ketones 55 (Scheme 3). To introduce a chiral center, compounds 55 were subjected to a condensation reaction with Ellman's sulfinamide as chiral ammonia equivalent in the presence of Ti(OiPr)4 as additive leading to N-sulfinyl imines 56.