Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

• Olesja Koleda,
• Janis Sadauskis,
• Darja Antonenko,
• Edvards Janis Treijs,
• Raivis Davis Steberis and
• Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

• 10.3762/bjoc.21.50 Abstract The electrochemical synthesis of 2-aminoprolines based on anodic decarboxylation–intramolecular amidation of readily available N-acetylamino malonic acid monoesters is reported. The decarboxylative amidation under Hofer–Moest reaction conditions proceeds in an undivided cell

• tetrahydropyran-containing amino acid derivatives via anodic decarboxylation of N-acetylamino malonic acid monoesters to generate a stabilized carbocation (Hofer–Moest conditions), which were then reacted with a tethered oxygen nucleophile [4]. In this follow-up study, we demonstrate that N-protected amines are

• in three steps (62% overall yield) from commercially available diethyl acetamidomalonate by an alkylation/hydrolysis/Boc-cleavage sequence (Scheme 1). The development of decarboxylative amidation commenced by examining the published conditions for anodic decarboxylation/etherification [4

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

• Matthias C. Letzel,
• Hans J. Schäfer and
• Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

• anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22–69% yield with a

• . Keywords: anodic decarboxylation; diastereoselectivity; Kolbe electrolysis; radical hetero-coupling; radical homo-coupling; Introduction Intermolecular radical additions with high diastereoselectivity have been described for a number of cases [1][2][3][4][5][6][7][8][9]. There are much fewer reports on

• ], and in intermolecular coupling of radicals generated by anodic decarboxylation of carboxylic acids [15][16]. At the anode radicals can be generated by anodic decarboxylation of carboxylic acids in molar quantities, in a simple procedure, unaffected by cage effects and in large diversity. For that