Gold-catalyzed chemo- and diastereoselective C(sp²)–H functionalization of enaminones for the synthesis of pyrrolo[3,4-c]-quinolin-1-one derivatives

Abstract

An efficient tandem Au(i)/TsOH-catalyzed reaction of enaminones with diazo compounds for the synthesis of pyrroloquinolinone derivatives under mild reaction conditions has been developed. This methodology was realized by relay actions of Au and TsOH in a one-pot multistep manner. Initially, the Au-catalyzed reaction of enaminones with diazo compounds affords chemo- and diastereoselective C(sp(2))-H functionalized products, which then undergo subsequent intramolecular cyclization/rearrangement to give pyrroloquinolinone derivatives under the catalysis of TsOH.