(S)-2-[(R)-fluoro(phenyl)methyl]oxirane: a general reagent for determining the ee of alpha-chiral amines |
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Authors: | Rodríguez-Escrich Sergi Popa Dana Jimeno Ciril Vidal-Ferran Anton Pericàs Miquel A |
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Institution: | Institute of Chemical Research of Catalonia (ICIQ), Av. Pa?sos Catalans s/n, 43007 Tarragona, Spain. |
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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] |
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