title: (S)-2-[(R)-fluoro(phenyl)methyl]oxirane: a general reagent for determining the ee of alpha-chiral amines.
abstract: (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]
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans s/n, 43007 Tarragona, Spain.
authors.forename: Sergi
authors.initials: S
authors.lastname: Rodríguez-Escrich
authors.forename: Dana
authors.initials: D
authors.lastname: Popa
authors.forename: Ciril
authors.initials: C
authors.lastname: Jimeno
authors.forename: Anton
authors.initials: A
authors.lastname: Vidal-Ferran
authors.forename: Miquel A
authors.initials: MA
authors.lastname: Pericàs