Catalytic Asymmetric Dihydroxylation of Enamides and Application to the Total Synthesis of (+)‐Tanikolide

Asymmetric dihydroxylation of β,β′- disubstituted enamides afforded chiral tertiary-alcohol-containing α-hydroxyaldehydes and 1,2-diols with high enantioselectivity (see scheme). This method was applied to the total synthesis of the antifungal natural product (+)-tanikolide, as well as the synthesis of an intermediate en route to (S)-oxybutynin.