Platinum(II) Salt Catalyzed Annulation of Hydroxyalkyl-Substituted Vinylsilanes with Aldehydes

Abstract

In the presence of catalytic amounts of PtCl2 and AgX (X = OTf or SbF6), (Z)-6-trimethylsilyl-5-hexen-1-ol and (Z)-5-trimethylsilyl-4-penten-1-ol reacted smoothly with aldehydes to give 2,3-disubstituted tetrahydropyrans and tetrahydrofurans, respectively, in good to high yields. The reaction mechanism involves the isomerization of the starting vinylsilanes to the corresponding allylsilanes and subsequence Prins-type annulation with aldehydes.