Asymmetric catalytic synthesis of lysine by hydrogenation of α-nitrocaprolactam

Autor: Klabunovskii, E. I., Gogoladze, D. D., Levitina, E. S., Karpeiskaya, E. I., Godunova, L. F., Kaigorodova, L. N., Chivadze, G. O.
Zdroj: Russian Chemical Bulletin; July 1987, Vol. 36 Issue: 7 p1475-1478, 4p
Abstrakt: Conclusions The enantioselective hydrogenation ofa-nitrocaprolactam (I) is effected on a chiral Pd complex, obtainedin situ in the presence of S-a-phenylethylamine, to give S-a-aminocaprolactam (II), hydrolysis of which gives S-lysine. The optical yield varies from 1 to 13% according to the solvent and concentration of chiral ligand. On a Pd complex with S-N-isopropyl-a-phenylethylamine, enantioselective hydrogenation of (I) gives an excess of the S-enantiomer of (II) (2%). On a Pd complex with S-phenylalaninol, hydrogenation of (I) leads to the R configuration of (II) with EE 7.2%.
Databáze: Supplemental Index