Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives:: Phenylalanine, tyrosine, histidine, and tryptophan

被引：50

作者：

Crich, David ^{[1
]}

Banerjee, Abhisek ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期

关键词：

ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALDOL REACTIONS; VANCOMYCIN; HYDROXYPHENYLALANINE; ANTIBIOTICS; ALDEHYDES; CHLORAMPHENICOL; TRANSFORMATION; REARRANGEMENT;

D O I：

10.1021/jo061159i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient synthesis of enantiomerically pure threo-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N, N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the, beta-hydroxy amino acid derivatives in excellent overall yield.

引用

收藏

页码：7106 / 7109

页数：4

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