We have developed a series of transition metal-catalyzed cross coupling reactions between propargylic alcohol derivatives and organometallic reagents to synthesize racemic allenes. Some of them could be applied for the chiral allene syntheses via the chirality transfer strategy utilizing optically pure propargylic alcohol derivatives. Now, we have been focusing on the development of catalytic asymmetric approaches for the chiral allene syntheses from racemic propargylic alcohols and derivatives.