Abstract
Conditions for fast racemization of 5(4H)-oxazolones prepared from N-acylphenylalanine were found. Reactions of 4-benzyl-2-methyl-5(4H)-oxazolone with amino acid esters proceed diastereoselectively to give predominantly dipeptides comprising R-phenylalanine. The diastereoselectivity increases with complication of the structure of the side chain in the amino acid esters.
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Krasnov, V.P., Zhdanova, E.A., Solieva, N.Z. et al. Study of the effect of the nature of the side chain in esters of α-amino acids on the diastereoselectivity of condensation with 5(4H)-oxazolone in the synthesis of dipeptides with N-terminal N-acetylphenylalanine. Russian Chemical Bulletin 53, 1331–1334 (2004). https://doi.org/10.1023/B:RUCB.0000042296.13831.bd
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DOI: https://doi.org/10.1023/B:RUCB.0000042296.13831.bd