The selective synthesis of cis-3,4-disubstituted pyrrolidines and piperidines is achieved by a Pd-catalyzed C–H arylation with excellent regio- and stereo-selectivity using an aminoquinoline auxiliary at C(3). The arylation conditions are silver free, use a low catalyst loading, and employ inexpensive K2CO3 as a base. Directing group removal is accomplished under new, mild conditions to access amide, acid, ester and alcohol containing fragments and building blocks. This C–H arylation protocol enabled a short and stereocontrolled formal synthesis of (–)-paroxetine.