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Preparation of α‐substituted α‐amino acids of high enantiomeric purity
Author(s) -
Pirkle William H.,
Heire Richard,
Hyun Myung Ho
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040508
Subject(s) - diastereomer , chemistry , enantiomer , isocyanate , hydrolysis , chiral derivatizing agent , enantiomeric excess , amino acid , organic chemistry , absolute configuration , chromatography , chiral column chromatography , enantioselective synthesis , catalysis , biochemistry , polyurethane
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.