Convenient synthesis of heterobicycles by domino Heck-Diels-Alder reactions

Abstract

Palladium(0)-catalyzed intramolecular cross coupling of bromodialkenylamines, bromoalkenylalkenamides and bromodialkenyl ethers followed by in situ [4+2] cycloaddition with suitable dienophiles gave tetrahydroisoindolines (31-73% yield), tetrahydroisoindolin-1-ones (43-51%) and hexahydrobenzo[c]furans (35-55%), and hexahydro-1H-[2]pyrindines (66-75%), respectively, each in one-pot operations.