The first electrocatalytic stereoselective multicomponent synthesis of cyclopropanecarboxylic acid derivatives

Abstract

The one-pot electrocatalytic domino transformation of aldehydes and two different C–H acids – alkyl cyanoacetate and dialkyl malonate in the presence of sodium bromide–sodium acetate as a double mediatory system in alcohol in an undivided cell (simple beaker) results in stereoselective formation of trialkyl(2R*,3R*)-3-aryl-2-cyanocyclopropane-1,1,2-tricarboxylates in 52–87% yields. This protocol uses group-assisted purification (GAP) chemistry in which the pure products were simply isolated by filtration from the reaction mixture. Developed electrocatalytic process allows to obtain multigramme-scale amount of trialkyl(2R*,3R*)-3-aryl-2-cyanocyclopropane-1,1,2-tricarboxylates.