Diastereoselective trifunctionalization of pyridinium salts to access structurally crowded azaheteropolycycles.

A highly diastereoselective dearomative trifunctionalization of pyridinium salts with multifunctional o-hydroxyl aromatic azomethine ylides has been established, which not only provided a convenient and rapid method to assemble challenging and architecturally crowded chroman-pyrrolidine-hydrogenated pyridine fused pentacycles, but also represented a rare successful example of the higher-order multifunctionalization of pyridiniums.