Entry to 2-Aminoprolines via Electrochemical Decarboxylative Amidation of N‑Acetylamino Malonic Acid Monoesters

Submitting author affiliation:
Latvian Institute of Organic Synthesis, Riga, Latvia

Beilstein Arch. 2024, 202471. https://doi.org/10.3762/bxiv.2024.71.v1

Published 19 Dec 2024

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Abstract

Electrochemical synthesis of 2-aminoprolines capitalizes on anodic decarboxylation-intramolecular amidation of readily available N-acetylamino malonic acid monoesters. The decarboxylative amidation under Hofer−Moest reaction conditions proceeds in an undivided cell under constant current conditions in aqueous acetonitrile and provides an access to N-sulfonyl, N-benzoyl, and N-Boc-protected 2-aminoproline derivatives.

Keywords: Anodic oxidation; decarboxylation; electrosynthesis; Hofer-Moest reaction; non-proteinogenic amino acids

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Koleda, O.; Sadauskis, J.; Antonenko, D.; Treijs, E. J.; Steberis, R. D.; Suna, E. Beilstein Arch. 2024, 202471. doi:10.3762/bxiv.2024.71.v1

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