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Vitamin B12 and a Vitamin B12 Model Compound as Catalysts of Reductive Removal of β-Haloethyl Protecting Groups from Acids

Authors

  • Prof. Dr. Rolf Scheffold,

    1. Institut für Organische Chemie der Universität, Freiestrasse 3, CH-3012 Bern (Switzerland)
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  • Dr. Erik Amble

    Corresponding author
    1. Institut für Organische Chemie der Universität, Freiestrasse 3, CH-3012 Bern (Switzerland)
    • Institut für Organische Chemie der Universität, Freiestrasse 3, CH-3012 Bern (Switzerland)
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  • Synthesis and Reactions of Porphinoid Metal Complexes, Part 9. This work was supported by the Schweizerischer Nationalfonds zur Förderung der wissen-schaftlichen Forschung (Projekt 2.151-0.78). We are grateful to Dr. P. Schneider, CIBA-GEIGY AG. Basel, for supplying penicillin V and its μ-haloethyl esters.—Part 8: [1].

Abstract

The transformation of β-chloroethyl esters (1) into acids (2) under extremely mild conditions, i.e. removal of the protecting group Cl(CH2)2[BOND], can be accomplished with zinc dust/NH4Cl or electrochemically. The catalyst is vitamin B12 or a model compound. Even lactam rings remain intact during the deprotection.

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