A CONVENIENT SYNTHESIS OF (S)-2-AZIDONITRILES, (S)-2-AMINONITRILES AND (S)-1,2-DIAMINES

(S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonylox y)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 und er complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 a nd by hydrogenation using LiAlH4 into (S)-1, 2-diaminoalkanes (S)-9, r espectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrol ysis of the aminonitrile hydrochlorides (S)-8 HCl in a saturated solut ion of HC1 in alcohol gives (S)-2-amino carboxamide hydrochlorides(S)- 10 . HCl with enantiomeric excesses >99% after recrystallization.