The atom‐ and step‐efficient synthesis of chiral fused tricyclic lactams from readily available ketoesters using cheap ammonium salts as the nitrogen source is reported. This ruthenium‐catalyzed system operates through an efficient tandem dynamic kinetic asymmetric reductive amination (ARA)/lactamization and produces chiral fused tricyclic lactams in high yields with excellent diastereo‐ and enantioselectivity (up to >99 % ee, >20 : 1 dr and 98 % yield). The robust method was also applied to the concise synthesis of key intermediates in the synthesis of rivastigmine analogues and chiral N‐heterocyclic carbene catalysts. An efficient and economical one‐pot approach to chiral fused tricyclic lactams from readily available ketoesters was developed by using cheap ammonium salts as the nitrogen source through ruthenium‐catalyzed tandem dynamic kinetic asymmetric reductive amination/lactamization. This protocol provides highly efficient access to drug intermediates and organocatalysts containing chiral polycyclic N‐heterocycles.