電子移動による活性種の生成の設計と制御

電極還元による活性塩基の生成とその有機合成への応用

抄録

Electrochemical reduction of 2-pyrrolidone in DMF using tetraalkylammonium salts (R₄NX) as supporting electrolytes yields the corresponding 2-pyrrolidone N-anion (PA). It is described in this article that the PA having R₄N⁺as the counter ion is highly useful as a base to promote a variety of base-catalyzed reactions which are not always easily achievable by using usual bases. Typical examples are as follows. (1) Formation of trihalomethyl anion (CX^-₃, X = Cl and F) from CHX₃ and their addition to aldehydes and α, β-unsaturated carbonyl compounds. (2) Esterification of carboxylic acids, and the synthesis of macrolides under very mild reaction conditions. (3) Selective C-alkylation of β-diketones. (4) Synthesis of α-alkylarylacetic acids which possess antiinflammatory and analgesic activities.