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

Oussema Ouerfelli | Zendy; Julien Simon | Zendy; Evelyne Chelain | Zendy; Julien Pytkowicz | Zendy; Rafâa Besbes | Zendy; Thierry Brigaud | Zendy

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

Author(s) -

Oussema Ouerfelli,

Julien Simon,

Evelyne Chelain,

Julien Pytkowicz,

Rafâa Besbes,

Thierry Brigaud

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00645

Subject(s) - enantiopure drug , aziridine , chemistry , oxazolidine , hydrolysis , yield (engineering) , strecker amino acid synthesis , cyanide , carboxylic acid , organic chemistry , amino acid , peptide , peptidomimetic , trifluoromethyl , combinatorial chemistry , enantioselective synthesis , biochemistry , catalysis , ring (chemistry) , materials science , alkyl , metallurgy

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.

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