Recent advances in the preparation of optically pure 1,2-diamines by stereoselective addition reactions to azomethine compounds (imines, iminium ions, oximes, hydrazones, nitrones). The methods scrutinized involve either the addition of carbon nucleophiles (organometallic reagents, carbanions, enolates, silyl enol ethers, carbon radicals and radical anions, too) to aldehyde derivatives, e.g. aldimines, and the complementary addition of hydrogen and hydride reagents to ketone derivatives, e.g. ketimines. Focus is given to the scope, advantages and limitations of the diverse methodologies and some possible developments are envisaged.