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Stereoselective synthesis of unsaturated α-amino acids

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Abstract

Stereoselective synthesis of unsaturated α-amino acids was performed by asymmetric alkylation. Two methods were investigated and their enantiomeric excess measured and compared. The first route consisted of an enantioselective approach induced by the Corey–Lygo catalyst under chiral phase transfer conditions while the second one involved the hydroxypinanone chiral auxiliary, both implicating Schiff bases as substrate. In all cases, the use of a prochiral Schiff base gave higher enantiomeric excess and yield in the final desired amino acid.

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Acknowledgments

We thank Géraldine Masson and Yan chao from ICSN for giving the Corey–Lygo catalyst and Medincell S.A for financial support (Cifre Grant of Adeline René).

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The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. IBMM, UMR-CNRS-5247, Universités Montpellier I and II, Place Eugène Bataillon, 34095, Montpellier, France

    Roberto Fanelli, Louis Jeanne-Julien, Adeline René, Jean Martinez & Florine Cavelier

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  1. Roberto Fanelli
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  2. Louis Jeanne-Julien
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  3. Adeline René
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  4. Jean Martinez
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  5. Florine Cavelier
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Correspondence to Florine Cavelier.

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Handling Editor: J. Leban.

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Fanelli, R., Jeanne-Julien, L., René, A. et al. Stereoselective synthesis of unsaturated α-amino acids. Amino Acids 47, 1107–1115 (2015). https://doi.org/10.1007/s00726-015-1934-0

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  • DOI: https://doi.org/10.1007/s00726-015-1934-0

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