A facile method for the chemodivergent synthesis of α-carbolines 1via palladium catalyzed [3+3] annulations of tosyliminoindolines 6 with α, β-unsaturated aldehydes 7 is described. Mechanistically, this cascade reaction proceeds through either a carba-Michael (in DMF) or aza-Michael (in NMA) pathway followed by intramolecular cyclization of the intermediate. A preliminary photo-physical study on selected products is also reported.