Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines

Abstract

A silver/palladium relay catalyzed 1,3-dipole annulation/allylation reaction of iminoesters and Baylis–Hillman acetates for the construction of fully substituted allyl imidazolidines is reported. The reaction of both iminoesters and Baylis–Hillman acetates affords the fully substituted allyl imidazolidines in high yields and regioselectivities. The three component reaction is triggered by silver-catalyzed 1,3-dipole annulation, followed by the sequential palladium catalyzed allylation. Mechanistic studies reveal that the dual catalytic system plays a key role in the reaction. The developed methodology provides straightforward access to allyl imidazolidines under simple reaction conditions.