Sequential Michael addition/retro-Claisen condensation of aromatic β-diketones with α,β-unsaturated esters: an approach to obtain 1,5-ketoesters.

Abstract

A K2CO3-catalyzed one-pot protocol involving sequential C-C bond formation and cleavage of aromatic β-diketones with α,β-unsaturated esters is developed to obtain 1,5-ketoesters. The sequential reaction via Michael addition and retro-Claisen condensation proceeds smoothly under mild conditions in up to 98% isolated yield. The mechanism study disclosed that the cascade process involved C-C bond cleavage of aromatic β-diketone as a phenacyl donor under alcoholic alkalescent conditions.