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Enantiopure α‑Trifluoromethylated Aziridine-2-carboxylic Acid (α-TfmAzy): Synthesis and Peptide Coupling

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journal contribution
posted on 27.03.2020, 17:37 by Oussema Ouerfelli, Julien Simon, Evelyne Chelain, Julien Pytkowicz, Rafâa Besbes, Thierry Brigaud
A straightforward synthesis of enantiopure α-trifluoromethyl aziridine-2-carboxylic acid (α-TfmAzy) is reported from a trifluoropyruvate derived enantiopure oxazolidine. A key Strecker-type synthetic step and a late cyanide basic hydrolysis gave the target compounds in six steps and 41% yield. A final peptide coupling was performed to demonstrate the usefulness of this highly constrained fluorinated unnatural amino acid.