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Preparation of α-substituted α-amino acids of high enantiomeric purity
Authors:William H Pirkle  Richard Heire  Myung Ho Hyun
Abstract:Racemic 5,5-dialkyl hydantoins derived from ketones are resolved by preparative liquid chromatography as the diastereomeric 1-carboxamide derivatives afforded by the reaction with optically pure configurationally known α-phenylethyl isocyanate. Hydrolysis of the resolved diastereomers affords α-substituted α-amino acids of high enantiomeric purity. The synthetic route is short, overall yields are high, and the absolute configuration of the amino acid enantiomers may be deduced from the chromatographic and NMR properties of the diastereomers. © 1992 Wiley-Liss, Inc.
Keywords:hydantoin derivatives  chiral isocyanates  LC separation of diastereomers  preparative LC separation
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