Asymmetric synthesis of amino acids by means of catalytic reduction of azlactones of substituted acylaminoacrylic acids Communication 13. Ammonolysis of 4-benzyl-5-oxazolone

Autor: Godunova, L. F., Levitina, E. S., Karpeiskaya, E. I., Klabunovskii, E. I., Lubuzh, E. D.
Zdroj: Russian Chemical Bulletin; August 1983, Vol. 32 Issue: 8 p1570-1575, 6p
Abstrakt: 1.Ammonolysis of 4-benzyl-5-oxazolone by S-(-)a-phenylethylamine in dimethoxyethane and in tertbutyl alcohol leads to the preferential formation ofa-phenylamide of the N-acylamino acid with the SS-configuration.2.We have shown the influence of the substituent in positions 2 and 4 and the influence of the nature of the solvent on the stereoselectivity of the process and on the rates of ammonolysis and racemization.3.We also show the possibility that ammonolysis can proceed in two directions: by the interaction of the neutral oxazol-5-one molecule with S-a-phenylethylamine and the interaction of the corresponding anion with S-a-phenylethylammonium.
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