In summary, we have demonstrated that ditert-butylsilanols are competent nucleophiles for the intramolecular interception of palladium π-allyl species. In these reactions, allyl ethyl carbonates were the best precursors for the formation of palladium π-allyl intermediates, and [(Cinnamyl)PdCl]2/BINAP was superior to other Pd salt/ligand framework combinations. Our optimized protocol was compatible with a variety of silanol substrates. Importantly, the cyclization is perfectly stereospecific, proceeding via an anti-syn mechanism. The alkenes in the product dioxasilinanes serve as blank slates for further functionalization, and we expect this reaction to be a useful addition to existing technology for the assembly of poly-hydroxylated targets.