Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols

Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable β-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction.