Small saturated heterocycles, namely tetrahydrofuran, pyrrolidine and thiolane derivatives, remain important targets in organic synthesis and drug design due to their prevalence as structural units in pharmaceuticals. One of the generally used strategies towards the synthesis of saturated heterocycles is intramolecular carbon-heteroatom bond formation, often requiring transition-metal catalysis in order to in situ generate the C(δ+) species, which is later trapped by an internal nucleophile. Alternatively, as a continuation to our previous work, we explored the possibility of generating stabilized carbocations via electrophilic activation of propargyl silanes. Electrophiles, such as H+, Br+, I+ and RSe+ readily added to the alkyne moiety in propargyl silanes, forming intermediate vinyl cations. Rapid 1,2-silyl migration yielded stabilized allylic cations, which were trapped by various internal O-, N- and S-nucleophiles, forming saturated heterocycles with highly stereodefined olefin side chain.