Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group. Benzyldimethylsilyl group as an effective promoter and novel hydroxy surrogate

A benzyldimethylsilyl (BnDMS) group was found to effectively enhance the reactivity of vinylsilanes toward the acid-catalyzed intramolecular addition of a hydroxy group in comparison with a dimethylphenylsilyl group. The BnDMS group of the resultant cyclized products could be easily converted to a hydroxy group by the action of TBAF–H2O2–KHCO3.