ChemInform Abstract: Asymmetric Synthesis of an Unusual Amino Acid: Synthesis of Four Isomers of β-Methyl-3-(2′-naphthyl)alanine.

✍ Scribed by W. YUAN; V. J. HRUBY

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199736225

✦ Synopsis

Asymmetric Synthesis of an Unusual Amino Acid: Synthesis of Four Isomers of β-Methyl-3-(2'-naphthyl)alanine.

-Using (R)-4phenyloxazolidinone (II) as chiral auxiliary, the synthesis of the optically pure amino acid (VIII) is achieved by diastereoselective methylation followed by indirect azidation and catalytic hydrogenation. The corresponding α-inverted diastereomer is accessible via direct azidation of (V) with trisyl azide. The preparation of the other pair of diastereomers starts from ( S)-(II). -(YUAN,