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(S)-α-methyl,α-amino acids: a new stereocontrolled synthesis

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Abstract

A new and convenient stereocontrolled synthesis of the optically pure (S)-α-methyl,α-amino acids 6(a–d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.

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Scheme 1
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Acknowledgments

Financial support was from the University of Bologna (RFO funds, ex 60%). The authors thank Prof. S. Sandri for the fundamental work developed in the research team for many years, particularly in the field of the asymmetric synthesis of natural and unnatural α-amino acids and pseudopeptides.

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Authors and Affiliations

  1. Dipartimento di Chimica “G.Ciamician”, Università di Bologna, Via Selmi 2, 40126, Bologna, Italy

    Daniele Balducci, Magda Monari & Gianni Porzi

  2. Dipartimento di Scienze Farmaceutiche, Università di Ferrara, Via Fossato di Mortara 17-19, 44100, Ferrara, Italy

    Ilaria Lazzari

  3. Laboratorio di Chimica dello stato solido DB, Università di Verona, Verona, Italy

    Fabio Piccinelli

Authors
  1. Daniele Balducci
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  2. Ilaria Lazzari
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  3. Magda Monari
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  4. Fabio Piccinelli
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  5. Gianni Porzi
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Correspondence to Daniele Balducci.

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Balducci, D., Lazzari, I., Monari, M. et al. (S)-α-methyl,α-amino acids: a new stereocontrolled synthesis. Amino Acids 38, 829–837 (2010). https://doi.org/10.1007/s00726-009-0289-9

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  • DOI: https://doi.org/10.1007/s00726-009-0289-9

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