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

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 under constant current conditions in aqueous acetonitrile and provides 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