A new type of δ-vinylvalerolactone for palladium-catalyzed cycloaddition: synthesis of nine-membered heterocycles

In this paper, a new type of -vinylvalerolactone was designed and synthesized, and used as a new precursor in Pd-catalyzed [6+3] cycloaddition with azomethine imines, leading to nine-membered 1,2-dinitrogen-containing heterocycles in 77-98% yields with >20: 1 d.r. These nine-membered ring-fused products were further transformed into unusual tetracyclic bridged-ring compounds without loss of the diastereoselectivities. A new type of precursor of zwitterionic allylpalladium intermediates for cycloaddition reactions was developed.