Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines and azabicyclo[3.2.2]nonanones

A palladium-catalyzed arylation/aza-Michael addition cascade reaction of beta-substituted cyclic enones and 2-haloanilines has been reported. Using 1 mol% Pd(PPh3)(4)as a catalyst, C2-spiroindolines are accessedviaan intermolecular vinylogous arylation of beta-alkyl cyclic enones and 2-haloanilines followed by an intramolecular aza-Michael addition. The functional group tolerance of this transformation is examined by 18 examples in up to 93% yield. In the second part, we developed an alpha '-arylation/aza-Michael addition cascade strategy to construct azabicyclo[3.2.2]nonanones catalyzed by Pd(MeCN)(2)Cl-2 center dot PPh3. This study provides a quick route to complex and useful spiro- and bridged-heterocycles from readily available starting materials in good yields with high regioselectivity.