Conclusions
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1.
Reductive aminolysis of 2-trifluoromethyl-4-benzylidene-Δ2-oxazolin-5-one in the presence of S-amino acid esters, PdCl2 and H2 proceeds via the intermediate formation of RS-peptides.
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2.
Aminolysis of 2-trifluoromethyl-Δ3-oxazolin-5-ones with S-AlaOMe, S-ValOMe, S-PheOMe proceeds with a high stereoselectivity, with the formation of SS-diastereomer, so that optically pure SS-PheAla and SS-PhePhe dipeptides could be obtained.
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3.
Aminolysis of 2-trifluoromethyl-Δ3-oxazolin-5-ones with S-ProOMe preferentially gives RS-peptides.
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Sh. G. Bitiev, G. V. Chel'tsova, E. I. Karpeiskaya, and E. I. Klabunovskii, Izv. Akad. Nauk, Ser. Khim., 2479 (1986).
E. G. Breitholle and G. H. Stammer, J. Org. Chem.,41, 1844 (1976).
M. R. Lyubeznova, K. V. Belyaeva, V. A. Ferapontov, E. I. Karpeiskaya, and E. I. Klavunovskii, Izv Akad. Nauk, Ser. Khim., 2482 (1984).
E. I. Karpeiskaya, L. F. Godunova, E. S. Levitina, M. R. Lyubeznova, E. I. Klabunovskii, E. D. Lubuzh, and A. I. Lutsenko, Izv. Akad. Nauk SSSR, Ser. Khim.,85 (1984).
W. Jenks, Catalysts in Chemistry and Enzymology [Russian translation], Mir, Moscow (1982), p. 350.
E. F. Schallenberg and M. Calvin, J. Am. Chem. Soc.,77, 2779 (1955).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 380–386, February, 1987.
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Bitiev, S.G., Chel'tsova, G.V., Lutsenko, M.R. et al. Catalytic asymmetric synthesis of dipeptides from 2-trifluoromethyl-Δ2- and 2-trifluoromethyl-Δ3-oxazolin-5-ones. Russ Chem Bull 36, 339–345 (1987). https://doi.org/10.1007/BF00959378
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DOI: https://doi.org/10.1007/BF00959378