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Diastereomeric Fluoroolefins as Peptide Bond Mimics Prepared by Asymmetric Reductive Amination of α-Fluoroenones

Guillaume Dutheuil 1 Samuel Couve-Bonnaire 1 Xavier Pannecoucke 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : Fluoropeptidomimetics: An efficient asymmetric reductive amination of fluoroenones has been developed that affords potential precursors of fluoropeptide isosteres. Stereoselective routes with different reductive agents provided both diastereomers from the same nonracemic sulfinyl imine. The method was applied to the synthesis of different dipeptide analogues.
Keywords : reductive amination peptidomimetics fluoroolefins fluoroenones asymmetric synthesis
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02384468
Contributor : Samuel Couve-Bonnaire <>
Submitted on : Thursday, November 28, 2019 - 1:45:36 PM
Last modification on : Tuesday, November 3, 2020 - 9:50:05 AM

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Guillaume Dutheuil, Samuel Couve-Bonnaire, Xavier Pannecoucke. Diastereomeric Fluoroolefins as Peptide Bond Mimics Prepared by Asymmetric Reductive Amination of α-Fluoroenones. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2007, 46 (8), pp.1290-1292. ⟨10.1002/anie.200604246⟩. ⟨hal-02384468⟩

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