Mechanistic Studies of the CuH-Catalyzed Synthesis of α-Hydroxyallenes

The copper hydride catalyzed S(N)2' reduction of propargyl oxiranes is an efficient method for the diastereoselective synthesis of alpha-hydroxyallenes. Herein, we represent a,detailed, computational study of this reaction using density functional theory (DFT), supported by kinetic investigations. The calculations partially validate the previously, proposed reaction mechanism and explain the high anti stereoselectivity of the reaction arising from a diffusion controlled Lewis acid activation of the epoxide-Cu-hydride complex.