(S)-2-[(R)-Fluoro(phenyl)methyl]oxirane: A General Reagent for Determining the ee of alpha-Chiral Amines

(S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution reagent, readily obtained from enantiopure (2S,3S)-phenylglycidol, that reacts with a variety of -chiral primary and secondary amines in a straightforward manner through a regioselective ring-opening. Diastereomeric products are easily identified and quantified by ¹⁹F, ¹H, and ¹³C NMR and by HPLC, which makes this fluorinated compound a most versatile reagent for the analysis of scalemic mixtures of amines.