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Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted acylaminoacrylic acids. 8. Reductive aminolysis of 4-isopropylidene-oxazol-5-ones

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

Conclusions

  1. 1.

    In the reaction of 4-isopropylideneoxazolones with S-(-)-α-phenylethylamine and hydrogen in the presence of a Pd catalyst in dimethoxyethane,α-phenylethylamide of N-benzoyl- or N-acetylvaline is obtained, preferentially in the SS-configuration, the N-acetyl derivative being formed with a higher stereoselectivity.

  2. 2.

    The reductive aminolysis process proceeds in the sphere of the catalytic complex, bypassing the stages of the formation of both unsaturated amide and saturated azlactone.

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Literature cited

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Authors and Affiliations

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

    G. V. Chel'tsova, E. I. Karpeiskaya & E. I. Klabunovskii

Authors
  1. G. V. Chel'tsova
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  2. E. I. Karpeiskaya
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  3. E. I. Klabunovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2350–2353, October, 1981.

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Chel'tsova, G.V., Karpeiskaya, E.I. & Klabunovskii, E.I. Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted acylaminoacrylic acids. 8. Reductive aminolysis of 4-isopropylidene-oxazol-5-ones. Russ Chem Bull 30, 1934–1937 (1981). https://doi.org/10.1007/BF00963427

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  • DOI: https://doi.org/10.1007/BF00963427

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