A practical synthesis of (2S,3R)-3-amino-2-methylpentanoic acid from L-aspartic acid

Article abstract of DOI:10.1002/hlca.19940770807

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%.