Abstract
Diastereoselective hydrogenation in ethanol over Pd/C ofN-acetyldehydrophenylalanyl-(S)-valine (1) as complexes with Mg salts of strong acids gives predominantlyN-acetyl-(S)-phenylalanyl-(S)-valine (de up to 60%). In the case of complexes of1 with Mg salts of weak acids, the sign of asymmetric induction changes. Data of19F NMR spectroscopy ofN-acetyldehydro(p-fluorophenylalanyl)-(S)-valine indicate that in the former case, the anion of a strong acid does not enter the coordination sphere of the complex, whereas in the larter case, the anion of the weak acid does. The nature of the solvent also influences the reaction stereoselectivity.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1704–1706, September, 1999.
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Lisichkina, I.N., Ushakova, O.M., Alekseeva, M.O. et al. The effect of anions in the coordination spherè of Mg complexes ofN-acetyldehydrophenylalanyl-(S)-valine on the diastereoselectivity of hydrogenation. Russ Chem Bull 48, 1682–1684 (1999). https://doi.org/10.1007/BF02494812
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DOI: https://doi.org/10.1007/BF02494812