This can easily done against a boss. Most other enemies would probably die too quickly, especially on low difficulties. Simply during a battle with a stronger enemy switch and use each turtle during the fight. You switch by holding
and then hitting the
.
for Michelangelo.
for Raphael.
For Donatello.
for Leonardo. If you've used all 4 during the battle the achievement will popped once the enemy is defeated. I made sure to strike the enemy with each turtle to be sure each counted toward the achievement but I don't know if that is truly needed.