Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome

Abstract

The gold-catalyzed intermolecular hydroalkylation of olefins with β-ketoesters represents a conceptually attractive and useful synthetic tool; however, it has been scarcely applied, remaining a challenge for chemists. The aim of the current study was to investigate the addition of these 1,3-diketo-compounds to alkenes under gold catalysis conditions, in order to establish the electronic and steric effects of the alkenyl substrates in the reaction outcome. The screening of different catalyst systems and diverse olefins enabled defining the alkenyl requirements and the best reaction conditions to efficiently achieve the coupled products.