We first examined N-Boc piperidine 4-carboxylic acid (isonipecotic acid) derivatives bearing bidentate directing groups. 27 Aminoquinoline amide 1 displayed the highest reactivity, and became the focus of our study. However under conditions previously reported for piperidines with a C(3) directing group, a mixture of four arylated products was observed (Table , entry 1). These were identified as mono-cis and mono-trans arylated piperidines 2a and 3a, as well as di-cis-trans and dicis-cis isomers 4a and 5a.