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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Bibliographic Details
Published inOrganic letters Vol. 6; no. 19; pp. 3233 - 3235
Main Authors Chen, Jason G, Zhu, Jingyang, Skonezny, Paul M, Rosso, Victor, Venit, John J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2004
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Crystallization
Indicators and Reagents
Molecular Structure
Phenylalanine - chemistry
Phenylpropionates - analysis
Phenylpropionates - chemical synthesis
Physical Sciences
Science & Technology
Stereoisomerism
PURE
INDUCED ASYMMETRIC TRANSFORMATION
RESOLUTION
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0489806