(E)-selective syntheses of Hemicurcuminoids/Styryl diketones by Wittig olefination of aromatic, cinnamic and aliphatic aldehydes

Abstract

In this work, we demonstrated a novel method for the synthesis of hemicurcuminods. The method is based on the Wittig olefination of aromatic, cinnamic and aliphatic aldehydes with 1-aryl-4-(triphenyl-λ⁵-phosphanylidene)butane-1,3-diones. This simple protocol has a broad aldehyde scope and great E-selectivity. The main advantage of this method is its ability to synthesize hemicurcuminoids containing acceptor groups and halogens in the styryl fragment with good yields. Hemicurcuminoids were obtained with a yield of up to 85 %. Moreover, this method can be easily scaled up for gram-scale synthesis of a wide scope of aromatic aldehydes.