Thioarylation of 6‐Amino‐2,3,6‐trideoxy‐d‐manno‐oct‐2‐ulosonic Acid (IminoKdo): Access to 3,6‐Disubstituted Picolinates and Mechanistic Insights
Sujit Manmode,
Nazar Hussain,
Oscar Javier Gamboa Marin
et al.
Abstract:In this work, we present a metal‐free coupling protocol for the regio‐ and stereoselective C3‐thioarylation of 6‐amino‐2,3,6‐trideoxy‐d‐manno‐oct‐2‐ulosonic acid (iminoKdo). The developed procedure enables the coupling of electron‐rich, electron‐deficient, and hindered arylthiols, providing a series of C3‐modified iminoKdo derivatives in moderate to good yields. Elucidation of active species through controlled experimental studies and time‐lapse 31P NMR analysis provides insights into the reaction mechanism. W… Show more
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