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. 2016 Feb 9;7(5):3406–3413. doi: 10.1039/c5sc04796j

Scheme 1. The reactions performed in this work from racemic mixtures of the 5(4H)-oxazolone enantiomers (l-2a and d-2a) with nucleophiles (NuH = H-l-Leu-NH2, H-l-Ala-NH2, H-Gly-NH2, or H-l-Leu-OH) in aqueous media, leading to the corresponding dipeptides as mixtures of enantiomers (Ac-l-Tyr(Me)-Gly-NH2 and Ac-d-Tyr(Me)-Gly-NH2) or diastereomers (Ac-l-Tyr(Me)-l-Leu-NH2 and Ac-d-Tyr(Me)-l-Leu-NH2, Ac-l-Tyr(Me)-l-Ala-NH2 and Ac-d-Tyr(Me)-l-Ala-NH2, or Ac-l-Tyr(Me)-l-Leu-OH and Ac-d-Tyr(Me)-l-Leu-OH). Although prepared from chiral Ac-l-Tyr(Me)-OH (l-1a), the oxazolone was present in a racemic state due to its chiral instability.36.

Scheme 1