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

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

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 fin...

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (8), p.2946-2949
Hauptverfasser: Ouerfelli, Oussema, Simon, Julien, Chelain, Evelyne, Pytkowicz, Julien, Besbes, Rafâa, Brigaud, Thierry
Format: Artikel
Sprache:eng
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Chemical Sciences
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00645