Palladium-Catalyzed Stereoselective Synthesis of 2-Allylpyrrolidines

Significance

A stereoselective synthesis of substituted pyrrolidines by the Pd-catalyzed reaction of γ-amino alkenes with vinyl and aryl bromides is reported. The sequence proceeds by an intramolecular C-N coupling followed by a sp³-sp² C-C coupling to provide products in reasonable to good yields and with high stereoselectivity. The sequence is also successful by inverting the procedure, i.e. initial coupling of the primary amine with the vinyl bromide and subsequent addition of the vinyl bromide.