Stereocontrol of cyclophane-type planar chirality was investigated via adsorption-induced asymmetric transformation (AIAT) on a series of inorganic porous adsorbents. The rope-skipping equilibria between bridged nicotinamides ( S,3′ S)- 1 and ( R,3′ S)- 2 shifted preferentially to ( R,3′ S)- 2 to accumulate ( R)-configuration of planar chirality with up to 61% de (ca. 4/1 ratio) on alumina. The results are in good contrast to accumulation of the corresponding ( S)-configuration via conventional crystallization-induced asymmetric transformation (CIAT) to the solid ( S,3′ S)- 1a– d .