Journal
ORGANIC LETTERS
Volume 23, Issue 2, Pages 382-387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03880
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- Agence Nationale de la Recherche
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The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline involves key steps such as Ruppert-Prakash reagent addition on L-pyroglutamic esters, followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on L-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
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