The synthesis of chiral mono- and bis-annelated 1,3-cyclopentadienes derived from tartaric acid, a chiral pool starting material, is described. In addition to known functionalized chiral 1,3-cyclopentadienes, new derivatives have also been structurally characterized by X-ray crystallographic and NMR spectroscopic studies. Neutral and cationic ruthenium(II) complexes, containing a mono-annelated chiral cyclopentadienyl ligand (1), have been successfully prepared. The X-ray crystal structure of [(eta(5)-Cp')Ru(eta(6)-benzene)][PF6], Cp'=1, has been determined.