The intramolecular bis-silylation of alkenes promoted by a palladium / tert-alkyl isocyanide is described. With disilanyl ethers derived from homoallylic alcohols, intramolecular bis-silylation proceeded with stereospecific cis-addition to give 5 exo-ring losure products. It is noteworthy that the bis-silylation of an alkene having an asymmetric center in the tether took place with high diastereoselection. Stereoselective synthesis of triols was carried out by oxidative cleavage of the Si-C bond thus formed. The reaction mechanism and synthetic application of the present bid-silylation will be discussed.