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
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概要
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Electrochemical reduction of 2-pyrrolidone in DMF using tetraalkylammonium salts (R<SUB>4</SUB>NX) as supporting electrolytes yields the corresponding 2-pyrrolidone <I>N</I>-anion (PA). It is described in this article that the PA having R<SUB>4</SUB>N<SUP>+</SUP>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<SUP>-</SUP><SUB>3</SUB>, X = Cl and F) from CHX<SUB>3</SUB> 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.
- 社団法人 有機合成化学協会の論文