A highly diastereoselective synthesis of spiroisoindolinones from enamides and 3-hydroxy-isoindolinones is reported. The reaction proceeds rapidly in the presence of p-toluenesulfonic acid as a Brønsted acid catalyst and affords a variety of densely substituted spiroisoindolinones with three contiguous stereogenic centers in high yields (≤98%) and diastereoselectivities (up to dr >98:<2:0:0).