Previously, we reported on the synthesis of lactams and other nitrogen heterocycles by the intramolecular cyclizations of carbamates and acyl derivatives of aminosulfones (Tetrahedron Lett. 2003, 44, 4035-4039). In an exciting and unexpected development , we have found that the imido sulfone derivatives I also undergo useful cyclization reactions upon treatment with LHMDS in THF at low temperatures. The intermediate alcohols obtained from these cyclizations upon dehydration gave the interesting bicyclic ring systems II in good yields. Our studies show that the highly functionalized heterocycle II is a valuable intermediate to access a wide array of other heterocyclic intermediates with control of stereochemistry. The preparation and cyclization reactions of I as well as the interesting synthetic potential of II will be discussed.