ChemInform Abstract: Electrochemically Initiated Tandem and Sequential Conjugate Addition Processes: One‐Pot Synthesis of Diverse Functionalized Isoindolinones.

Abstract

Functionalized Isoindolinones. -Synthesis of highly functionalized 3-isoindolinones is achieved by the present new electroreductively-catalyzed reaction of 1,3-dicarbonyl compounds with cyanobenzaldehyde (I). The desired products are obtained under mild conditions and in short reaction times by galvanostatic electrolysis in a divided cell. In contrast, cyclohexanedione (XI) gives product (XII) instead of the desired product due to electro-initiated Knoevenagel-Michael reaction. Isoindolines (III) and (XIV) subsequently undergo Michael addition with acrylates (IV) or, this reaction is performed in one pot giving functionalized adducts (V) and (XIV), respectively. Furthermore, additional Michael reaction with acrolein (VI) gives novel tricyclic isoindolines like (VII) with high diastereoselectivity. -(ANTICO, P.; CAPACCIO, V.; DI MOLA, A.; MASSA*, A.; PALOMBI, L.; Adv. Synth. Catal. 354 (2012) 9, 1717-1724, http://dx.