Efficient asymmetric synthesis of 1-alk-2-yne-1,4-diols

We describe an expeditious process that provides ready access to symmetrical and unsymmetrical optically active bispropargylic 1,4-diols. The method employs the use of a recent method we have developed involving terminal acetylenes, Zn(OTf)2, amine base, and N-methyl ephedrine. The 1,4-diol products should serve as useful building blocks for asymmetric synthesis.