Chiral polyamines can be utilized for a variety of potential applications, ranging from asymmetric catalysis to nonviral gene delivery systems for DNA and RNA. They can also be utilized to solubilize carbon nanotubes. Thus, methods for the straightforward synthesis of chiral polyamines are needed. We present herein two synthetic strategies for accessing chiral polyamines. One strategy leads to polyethyleneglycol � chiral polyamine block copolymers, and the other leads to well-defined oligo-amines from the reduction of chiral polypeptides. The potential of these chiral amines to catalyze two organic reactions with a high degree of chiral induction is also explored.