The systematic investigation of substrate-bound alpha-amino acid auxiliaries has resulted in catalytic asymmetric C-H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH2 auxiliary embedded in the substrate provided excellent levels of asymmetric induction (diastereomeric ratio of up to 72:1) in the Pd(II)-catalyzed beta-methylene C(sp(3))-H bond activation of cyclopropanes and cross-coupling with aryl iodides.