Preparation of (S)-2-fluoronitriles

Abstract

(S)-2-fluoronitriles (S)-4 are obtained in good chemical and high optical yields from (R)-cyanohydrins (R)-2 or (R)-cyanohydrin trimethylsilylethers (R)-3 by fluorination with DAST or by nucleophilic substitution of α-sulfonyloxynitriles (R)-6,7 with fluoride on polymeric supports (Amberlyst A-26 F−) under inversion of configuration of the starting cyanohydrins.