Methods to diversify indolizines are valuable for the discovery of medications and fluorescent molecules. The utilization of copper-catalyzed asymmetric propargylation to install a terminal alkyne handle on indolizine heterocycle is reported. This method delivers C3-propargylation products from C2-substituted indolizines or C1-propargylation products from C2,C3-disubstituted indolizines through a stereoconvergent pathway.