The concept described the development of a chiral acetal?based stereo?controlled degradable polymer, which was prepared via living cascade enyne metathesis polymerization with the controlled addition of highly stereodefined N,O?acetal?containing enyne monomers from Pd?catalyzed asymmetric hydroamination of alkoxyallene and ring?closing metathesis.The precise synthesis of chiral polymers remains a significant challenge in polymer chemistry, particularly for applications in advanced biomedical and electronic materials. The development of degradable polymers is important for eco?friendly and advanced materials. Here, we introduce a stereo?controlled degradable polymer via cascade enyne metathesis polymerization and enantioselective acetal synthesis through Pd?catalyzed asymmetric hydroamination. This approach allows for the creation of chiral acetal?based polymers with controlled stereochemistry and degradability, highlighting their potential for use in drug delivery and electronic applications. This concept article reviews the background, development, and potential applications of these stereo?controlled degradable polymers.