High enantioselectivity was achieved for the hydrogenation of azaindoles by using the chiral catalyst, whichw as prepared from [Ru(h 3 -methallyl) 2 (cod)] and at rans-chelating bis(phosphine) ligand (PhTRAP). The dearomative reaction exclusively occurred on the five-membered ring, thus giving the corresponding azaindolines with up to 97:3 enantiomer ratio.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.