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A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines

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Abstract

Straightforward preparation of enantiomerically highly enriched N-substituted aroylalanines has been developed. This process involves the combination of crystallization-induced asymmetric transformation and a conjugate addition of N-nucleophiles to the corresponding aroylacrylic acids. Further transformations to 3,4-dichlorobenzoylalanine and aroyl-l-alanines via periodate oxidation and stereoselective reduction to N-substituted syn-4-aryl-4-hydroxy-2-aminobutanoic acids are also described.

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Authors and Affiliations

  1. Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Mária Gardiánová, Ľuboš Slížik, Anna Koreňová, František Považanec & Dušan Berkeš

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  1. Mária Gardiánová
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  2. Ľuboš Slížik
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  3. Anna Koreňová
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  4. František Považanec
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  5. Dušan Berkeš
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Correspondence to Dušan Berkeš.

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Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

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Gardiánová, M., Slížik, Ľ., Koreňová, A. et al. A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines. Chem. Pap. 67, 92–100 (2013). https://doi.org/10.2478/s11696-012-0246-z

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  • DOI: https://doi.org/10.2478/s11696-012-0246-z

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