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  • Title: Crystallization-induced chiral inversion as the key step for synthesis of (S)-2-acetylthio-3-phenylpropanoic acid from l-phenylalanine.
    Author: Chen JG, Zhu J, Skonezny PM, Rosso V, Venit JJ.
    Journal: Org Lett; 2004 Sep 16; 6(19):3233-5. PubMed ID: 15355020.
    Abstract:
    [reaction: see text] 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.
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