An enantioselective nickel(0)-catalyzedC  Hfunc- tionalization of indoles and pyrroles that does not require the typical Lewis basic directing groups is disclosed. The reaction provides access to valuable tetrahydropyridoindoles and tetrahydroindolizines in high yields and enantioselectivity under mild reaction conditions.The process is characterized by aclear endo-cyclization preference to yield the sought-after six-membered-ring products.Key for the success of the activation and selectivity in the cyclization was the develop- ment of anovel chiral SIPr carbene ligand analogue with very bulky flanking groups.