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Chiral nucleophilic glycine and alanine synthons: nickel(II) complexes of Schiff bases of (S)-N-(2,4,6-trimethylbenzyl)proline (2-benzoylphenyl)amide and glycine or alanine

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Abstract

A new chiral auxilliary, (S)-N-(2,4,6-trimethylbenzyl)proline (2-benzoylphenyl)amide, has been synthesised as a potential building block for the preparation of chiral synthons of amino acids. The nickel(II) complex of its Schiff base derivative with glycine has been methylated with 97% d.e. (diastereomeric excess), whilst the nickel(II) complex of its Schiff base derivative with (RS)alanine has been 13C-methylated with 66% d.e.

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Author notes

  1. Alexander Popkov

    Present address: University of South Bohemia, Nový Zámek, Zámecká 136, 373 33, Nové Hrady, Czech Republic

Authors and Affiliations

  1. Positron Emission Tomography Centre, Aarhus University Hospital, Nørrebrogade 44, 8000, Aarhus C, Denmark

    Alexander Popkov

  2. 8000 Aarhus C, Denmark; Present address: GlaxoSmithKline, Addenbrooke's Center for Clinical Investigation, Addenbrooke's Hospital, Cambridge CB2 2GG, UK

    Antony Gee

  3. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, 532 10, Pardubice, Czech Republic

    Milan Nádvorník

  4. Research Institute for Organic Syntheses, 532 18, Pardubice-Rybitví, Czech Republic

    Antonín Lyčka

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  1. Alexander Popkov
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  3. Milan Nádvorník
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  4. Antonín Lyčka
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Popkov, A., Gee, A., Nádvorník, M. et al. Chiral nucleophilic glycine and alanine synthons: nickel(II) complexes of Schiff bases of (S)-N-(2,4,6-trimethylbenzyl)proline (2-benzoylphenyl)amide and glycine or alanine. Transition Metal Chemistry 27, 884–887 (2002). https://doi.org/10.1023/A:1021361330364

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