Base-catalyzed annulation reactions of 5,6-dihydro-2(1H)-pyridones with Nazarov-type reagents are reported. The effect of the solvent polarity and the concentration of the reagents is studied. The process involves two successive Michael additions and stereoselectively provides functionalized cis-perhydroisoquinolin-1-ones.
Keywords: 5,6-dihydro-2(1H)-pyridone; Michael addition; Nazarov reagents; perhydroisoquinoline; stereoselectivity.