A convenient synthesis of (S)-2-azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines

Article abstract of DOI:10.1016/0957-4166(96)00044-4

(S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH₄ into (S)-1,2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8·HCl in a saturated solution of HCl in alcohol gives (S)-2-amino carboxamide hydrochlorides (S)-10·HCl with enantiomeric excesses >99% after recrystallization.