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Twelve optically active metallocene complexes of Ca, Sm(II), and Yb(II) containing cyclopentadienyl systems with a chiral N-or O-substituted side chain as ligands are described. Specifically, the ligand systems (S)-( 2systems were employed. The starting materials for their synthesis are ethyl (S)-(-)-lactate, (R)-(-)-2-methoxy-2-phenylethanol, (S)-(+)-2-amino-1-propanol, and (R)-(-)-2-phenylglycinol, respectively. Each of the cyclopentadienyl systems was converted by a 2:1 reaction of the potassium salt with the metal diiodide into the corresponding metallocene, [M{(S)-η 5 :η Sm (2b), Yb (2c)), and [M{(S)-η 5 :η 1 -C 5 H 4 (CH(Ph)CH 2 NMe 2 )} 2 ] (M ) Ca (4a), Sm (4b), Yb (4c)). The novel compounds have been characterized by C, H, N analysis, mass spectrometry, NMR spectroscopy, and optical rotation. Additionally, an X-ray structural analysis of 2c, 3a, and 4a was performed.

2 [TmI 2 (dme) 3 ] + 4 LiC 10 H 8 dme, 20 °C [{Tm(dme)} 2 (C 10 H 8 ) 3 ] + 4 LiI + C 10 H 8 1, 92% C(11′) C(11) C(12) C(15) C(13) C(14) Tm O(2) C(19) C(18) C(17) O(1) C(16) C(4) C(3) C(2) C(1) C(10) C(5) C(6) C(9) C(8) C(7)

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