Gold-Catalyzed Bicyclic Annulations of N -( o -Alkynylphenyl)imines with α-Diazo Esters to Form 5,6-Dihydroindolo[2,1- a ]isoquinolines.

One-pot synthesis of 5,6-dihydroindolo[2,1- a ]isoquinolines from gold-catalyzed annulations between N -( o -alkynylphenyl)imines and α-diazo esters is described. This cascade reaction involves an initial attack of the diazo ester at the imine to form cis -aziridine, followed by stereoselective [3 + 3]-annulations with the tethered arylalkyne. We have employed this new catalysis to prepare one bioactive 5,6-dihydroindolo[2,1- a ]isoquinoline molecule.