Chelating Carboxylic Acid Amides as Robust Relay Protecting Groups of Carboxylic Acids and their Cleavage under Mild Conditions

Authors

  • Dipl.-Chem. Manuel C. Bröhmer,

    1. Institute of Organic Chemistry, KIT-Campus Süd, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany)
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  • Stephan Mundinger,

    1. Institute of Organic Chemistry and Biochemistry, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg (Germany), Fax: (+49) 761-203-8705
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  • Prof. Dr. Stefan Bräse,

    1. Institute of Organic Chemistry, KIT-Campus Süd, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany)
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  • Prof. Dr. Willi Bannwarth

    Corresponding author
    1. Institute of Organic Chemistry and Biochemistry, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg (Germany), Fax: (+49) 761-203-8705
    • Institute of Organic Chemistry and Biochemistry, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg (Germany), Fax: (+49) 761-203-8705
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  • We thank Prof. Dr. C. C. Tzschucke for helpful discussions. M.C.B. thanks the Landesgraduiertenförderung Baden-Württemberg for a PhD fellowship and Feasibility Studies of Young Scientists—KIT for generous financial support.

Abstract

original image

Free choice: Carboxamides of bispicolylamine are alternative protecting groups for carboxylic acids (see scheme). As a consequence of their straightforward applicability, their high chemical stability towards a broad range of conditions, and their selective cleavage under mild conditions to give either carboxylic acids or their methyl esters, this new protection method should find widespread application in the realm of organic synthesis.

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