Nitroalkanes as alkyl anion synthons - a new approach to the synthesis of 2-substituted n-ethyl succinimides and 2-substituted succinate diesters via nitroalkanes

Abstract

2-Substituted N-ethyl succinimide and 2-substituted succinate diesters were obtained by two key steps: (i) Michael addition of a nitroalkane to the appropriate enedione derivative under basic conditions (DBU), with the concomitant elimination of nitrous acid, and (ii) selective reduction of the obtained enone with nickel boride, in methanol/THF. In this context the nirtoalkane acts as an alkyl anion synthon. By this method trimethyl tricarboxylates were also synthesized.