PREPARATION OF ALPHA-SUBSTITUTED ALPHA-AMINO-ACIDS OF HIGH ENANTIOMERIC PURITY

被引：3

作者：

PIRKLE, WH ^{[1
]}

HEIRE, R ^{[1
]}

HYUN, MH ^{[1
]}

机构：

[1] PUSAN NATL UNIV,DEPT CHEM,PUSAN,SOUTH KOREA

来源：

CHIRALITY | 1992年 / 4卷 / 05期

关键词：

HYDANTOIN DERIVATIVES; CHIRAL ISOCYANATES; LC SEPARATION OF DIASTEREOMERS; PREPARATIVE LC SEPARATION;

D O I：

10.1002/chir.530040508

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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 alpha-phenylethyl isocyanate. Hydrolysis of the resolved diastereomers affords alpha-substituted alpha-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.

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页码：302 / 307

页数：6

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