Catalytic multicomponent [m + n + o]-type cycloadditions offer efficient, atom-economical routes to diverse complex carbocycles. Recently, such transformations have emerged as unique strategies for medium ring carbocycle synthesis. Despite the important developments in this area, however, highly enantioselective [m + n + o]-type processes accessing medium ring carbocycles have yet to be developed. Herein, a rhodium-catalyzed [4 + 2 + 2] cycloaddition of allenedienes with allenes enabling the direct stereoselective synthesis of cis-fused cyclooctanoids is reported. These cycloadditions are successful with a diverse range of π-components and demonstrate the potential for high levels of enantioselectivity in a [4 + 2 + 2] process.