Uhm he did when Itachi showed him his parents and clans murder via genjutsu. He got his first Tomoe. Then his second Tomoe when they faced Haku, and the third at VOTE I.
But ur right in some sense i feel like he would awaken 3 tomoe or even MS because his own brother that he loved slaughtered his whole family and parents thats worst then gaining ms by killin your bestfriend tbh