S-Methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1掳-尾-C(sp3)鈥揌 bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd(II)-catalyst. The sequential halogenation and acetoxylation of 伪-dimethyl MPyS-N-amides constructs highly functionalized 伪-trisubstituted aliphatic acid derivatives. The MPyS directing group is cleaved from the halogenated products and recovered.