(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 alpha-chiral primary and secondary amines in a straightforward manner through a regioselective ring-opening. Diastereomeric products are easily identified and quantified by (19)F, (1)H, and (13)C NMR and by HPLC, which makes this fluorinated compound a most versatile reagent for the analysis of scalemic mixtures of amines. [reaction: see text]
Rodríguez-Escrich
Sergi
S
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans s/n, 43007 Tarragona, Spain.
Popa
Dana
D
Jimeno
Ciril
C
Vidal-Ferran
Anton
A
Pericàs
Miquel A
MA