Asymmetric synthesis by catalytic reductive aminolysis of p-fluoro-α-acetaminocinnamic acid azalactone. Communication 18. Preparation of S-(-)-p-fluorophenylalanine

Autor: Godunova, L. F., Karpeiskaya, E. I., Levitina, E. S., Klabunovskii, E. I., Yagupol'skii, Yu. L., Kolycheva, M. T.
Zdroj: Russian Chemical Bulletin; June 1987, Vol. 36 Issue: 6 p1254-1256, 3p
Abstrakt: 1.In reductive aminolysis of p-fluoroacetaminocinnamic acid azalactone by S-(-)-a-phenylethylamine in the presence of PdCl2 and H2 in dimethoxyethane or isopropyl alcohol, N-acetyl-p-fluorophenylalanine phenylethylamide was formed with 28 and 46% excesses of the SS diastereomer, respectively, the hydrolysis of which, after crystallization, afforded optically pure S-(-)-p-fluorophenylalanine.2.Hydrogenation of p-fluoroacetaminocinnamic acid S-(+)-phenylethylamide in isopropyl alcohol and dimethoxyethane occurred stereoselectively and afforded N-acetyl-p-fluorophenyl-alanine phenylethylamide with 10% excess of the RS diastereomer.
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