Abstract A new stereoselective synthesis of both (2 R ,4 R )- and (2 S ,4 S )-4-hydroxy-proline and (+)- and (−)-bulgecinine was performed starting from synthons 1 or 1′ , respectively. The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2).