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

Abstract

(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 LiAlH 4 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. O -sulfonylated ( R )-cyanohydrins 2,5 react with azides to give ( S )-2-azidonitriles 4 which can be converted without racemization into ( S )-2-aminonitriles 8 , ( S )-1,2-diaminoalkanes 9 and ( S )-2-amino carboxamides 10 , isolated as hydrochlorides.