Abstract: A chiral imidazolinium 3-oxide has been prepared, that undergoes diastereoselective dipolar cycloaddition with alkenes to afford imidazo [1, 2-b] isoxazoles; a suitable cycloadduct undergoes NO cleavage and recyclisation leading to a pyrrolo [1, 2-a] imidazole and thence potentially to pyrrolidines. Key words: imidazoisoxazoles, nitrones, cycloadditions, heterocycles, bicyclic compounds