Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate

Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.