A PRACTICAL SYNTHESIS OF (2S,3R)-3-AMINO-2-METHYLPENTANOIC ACID FROM L-ASPARTIC ACID

被引:25
作者
JEFFORD, CW
MCNULTY, J
机构
[1] Department of Organic Chemistry, University of Geneva, Geneva
关键词
D O I
10.1002/hlca.19940770807
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
L-Aspartic acid by successive N-tosylation, anhydride formation, and reduction was converted into (3S)-3-(tosylamino)butano-4-lactone (4). Electrophilic methylation of 4, subsequent iodo-esterification and nucleophilic methylation, followed by saponification and deprotection, gave (2S,3R)-3-amino-2-methylpentanoic acid (2) with an ee of > 99 % in seven steps and in an overall yield of 34%.
引用
收藏
页码:2142 / 2146
页数:5
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