Journal
ORGANIC LETTERS
Volume 22, Issue 8, Pages 2946-2949Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00645
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A straightforward synthesis of enantiopure alpha-trifluoromethyl aziridine-2-carboxylic acid (alpha-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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