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Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted N-acylaminoacrylic acids Communication 15. Influence of nucleophilic additives on mechanism of reductive aminolysis of Δ2-oxazolin-5-ones

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The opening of S-2-methyl-4-benzyloxazol-5-one by nucleophiles N-OSI and N-OBT In dioxane in t-BuOH leads to the formation of optically active esters of S-acetylphenylalanine.

  2. 2.

    The reductive aminolysis of Δ2-oxazolin-5-ones in the presence of PdCl2, S-α-phenylethylamine and N-OSI or N-OBT leads to the formation of amides of N-acylamino acids with a ratio of diastereomers RS∶SS=1∶1.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    L. N. Kaigorodova, E. S. Levitina, E. I. Karpeiskaya & E. I. Klabunovskii

Authors
  1. L. N. Kaigorodova
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  2. E. S. Levitina
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  3. E. I. Karpeiskaya
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  4. E. I. Klabunovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 813–816, April, 1984.

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Kaigorodova, L.N., Levitina, E.S., Karpeiskaya, E.I. et al. Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted N-acylaminoacrylic acids Communication 15. Influence of nucleophilic additives on mechanism of reductive aminolysis of Δ2-oxazolin-5-ones. Russ Chem Bull 33, 747–749 (1984). https://doi.org/10.1007/BF00947825

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  • DOI: https://doi.org/10.1007/BF00947825

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