Dissertation is focused on synthesis of enantiomerically pure 1,3–diamines and their application in enantioselective protonation of lithium enolates. A methodology for stereoselective synthesis of chiral non-racemic 1,3-diamines has been developed based on a highly diastereoselective reduction of N-tert- butanesulfinylimines. A correlation between structure of N-tert-butanesulfinylimines (E/Z and M/P geometries) and sense of asymmetric induction in their reduction has been established. E/Z And M/P geometries of N-tert-butanesulfinylimines were determined both in crystalline form (by X-ray crystallographic analysis) and in THF– d8 solution (by NMR methods). Rate constants for E/Z isomerization and M/P atropisomerization as well as the corresponding Gibbs free energies of activation for isomerization were determined. Synthesized chiral non-racemic 1,3-diamines have been employed as chiral proton sources in enantioselective protonation of naproxen–derived lithium enolates. A relationship between steric hinderance of 1,3-diamines and enantioselectivity of proton transfer was studied. A principal chiral subunit in a 1,3-diamine, which ensures discrimination of enolate enantiotopic faces has been established.