Catalytic Enantioselective Syn-Hydroxy-Oxyacylation of Electron Deficient Alkenes

Asymmetric syn-dihydroxylation and dioxyacylation of alkenes have been well established. A direct method for the enantioselective preparation of orthogonally protected syn-1,2-diols from alkenes is unprecedented. Here in, we report the first enantioselective hypervalent iodine catalyzed syn-hydroxy-oxyacylation of enones. The orthogonally protected diols were obtained with excellent diastereo- and regioselectivity under metal-free condition. For these electron-deficient alkenes, even the syn-dihydroxylation and dioxyacylation have remained yet an unfinished challenge.