Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.