Crystallization-Induced Chiral Inversion As the Key Step for Synthesis of (S)-2-Acetylthio-3-phenylpropanoic Acid from l-Phenylalanine

Crystallization-Induced Chiral Inversion As the Key Step for Synthesis of (S)-2-Acetylthio-3-phenylpropanoic Acid from l-Phenylalanine

A novel crystallization-induced chiral inversion of (S)-2-bromo-3-phenylpropanoic acid to its (R)-enantiomer with excellent enantiomeric excess (96−99%) is achieved. Optically pure (S)-2-acetylthio-3-phenylpropanoic acid can be prepared in good yield from inexpensive and commercially available l-phe...

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Veröffentlicht in:Organic letters 2004-09, Vol.6 (19), p.3233-3235
Hauptverfasser: Chen, Jason G, Zhu, Jingyang, Skonezny, Paul M, Rosso, Victor, Venit, John J
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Crystallization
Indicators and Reagents
Molecular Structure
Phenylalanine - chemistry
Phenylpropionates - analysis
Phenylpropionates - chemical synthesis
Stereoisomerism
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Beschreibung
Zusammenfassung:A novel crystallization-induced chiral inversion of (S)-2-bromo-3-phenylpropanoic acid to its (R)-enantiomer with excellent enantiomeric excess (96−99%) is achieved. Optically pure (S)-2-acetylthio-3-phenylpropanoic acid can be prepared in good yield from inexpensive and commercially available l-phenylalanine via diazotization/bromination, chiral inversion, and thioacetate substitution reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0489806