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Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-α-amino acids

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Abstract

The synthesis of new chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(3,4-dichlorobenzyl)-pyrrolidine-2-carboxamide (1a), (S)-N-(2-benzoylphenyl)-1-(pentafluorobenzyl)pyrrolidine-2-carboxamide (1b), and (S)-N-(2-benzoylphenyl)-1-(4-isopropoxytetrafluorobenzyl)pyrrolidine-2-carboxamide (1c) and their application in the asymmetric synthesis of amino acids using NiII complexes of their Schiff"s bases with alanine and glycine are described. Compound 1a is particularly appropriate for highly stereoselective synthesis of α-methyl-α-amino acids with high enatiomeric purity (ee >95%).

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Authors and Affiliations

  1. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Yu. N. Belokon, V. I. Maleev, T. F. Savel"eva, N. S. Ikonnikov, A. S. Peregudov & V. N. Khrustalev

  2. Research Institute of Biotechnology of the Ministry of Industry of Republic Armenia, 14 ul. Gjurdjan, 375056, Yerevan, Republic Armenia

    A. A. Petrosyan & A. S. Saghiyan

Authors
  1. Yu. N. Belokon
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  2. V. I. Maleev
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  3. A. A. Petrosyan
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  4. T. F. Savel"eva
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  5. N. S. Ikonnikov
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  6. A. S. Peregudov
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  7. V. N. Khrustalev
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  8. A. S. Saghiyan
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Belokon, Y.N., Maleev, V.I., Petrosyan, A.A. et al. Halo-substituted (S)-N-(2-benzoylphenyl)-1-benzylpyrolidine-2-carboxamides as new chiral auxiliaries for the asymmetric synthesis of (S)-α-amino acids. Russian Chemical Bulletin 51, 1593–1599 (2002). https://doi.org/10.1023/A:1020952115556

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