A highly regioselective azidolysis of 2,3-epoxy amines: an unexpected Ti(O-i-Pr)2(N3)2 mediated C-2 opening

The Lewis acid-catalyzed regioselective azidolysis of 2,3-epoxy amines has been investigated. The results obtained demonstrated that using TMSN3 as a source of azide, the appropriate choice of Lewis acid allowed to direct the regiochemistry of the ring opening. The present methodologies provide a powerful tool in organic synthesis for the preparation of diaminoalcohol moieties.