A Practical Synthesis of (2S, 3R)‐3‐Amino‐2‐methylpentanoic Acid from L‐Aspartic Acid Journal Articles uri icon

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abstract

  • AbstractL‐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%.

publication date

  • December 14, 1994