N-protected amino acid and dipeptide branched, chiral polyolefins have been prepared using acyclic diene metathesis polycondensation chemistry. The polymerizations were performed in THF using Grubbs' second-generation catalyst. The polymers bearing CBz-protected amino acids and dipeptides are semicrystalline with melt transitions of up to 150 degreesC, whereas the polymers bearing BOC-protected amino acids and dipeptides are primarily amorphous with the exception of the di-BOC-protected lysine polymer, which is semicrystalline.