The enantioselective synthesis of planar chiral [7] and [8]paracyclophanes has been achieved by the cationic rhodium(I)-(S)-H8-BINAP complex catalyzed [2+2+2] cycloaddn. Planar chiral [9]paracyclophanes were also synthesized by the same method. The X-ray crystallog. anal. of the strained dioxa[7]paracyclophane revealed the significant deformation of the benzene ring from planarity. [on SciFinder(R)]