Vinylogous Intramolecular Rauhut–Currier Reaction Using Styrene Derivatives as Terminal Pseudo-Michael Acceptors

An intramolecular vinylogous Rauhut–Currier reaction has been achieved using vinyl arenes as a terminal pseudo-Michael acceptor. Sluggish acrylamide successfully acted as a source of initial enolate. An organocatalytic alkene functionalization via benzylic stabilization of anion was achieved from a remotely located EWG. Various EWGs and even heteroaryl moieties from various positions were applicable. Pleasingly, the present toolbox leads to the synthesis of functionalized quinolone/piperidone derivatives.