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.