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2004
C-C bond formation
O 0282
Regulation of the Flexibility of Planar Chiral [2.2]Paracyclophane Ligands and
Significant Impact on Enantioselectivity in Asymmetric Reactions of Diethyl51- 050 Its
zinc with Carbonyl Compounds. — A series of new planar chiral N,O-ligands is synthesized and applied as catalysts in enantioselective additions of diethylzinc to aldehydes and α,β-ketones. The effect of the rigidity and flexibility of the ligands on the
enantioselectivity of the addition reactions as well as the role of their planar chirality
in these reactions are investigated. Ligand (Ia) with a dimethyl hydroxymethyl substituent gives the best results (up to 98% e.e.) in the addition of diethylzinc to aldehydes
while in the addition to chalcones excellent enantioselectivities (up to 83% e.e.) are obtained using ligand (Ib). — (WU, X.-W.; ZHANG, T.-Z.; YUAN, K.; HOU*, X.-L.;
Tetrahedron: Asymmetry 15 (2004) 15, 2357-2365; State Key Lab. Organomet.
Chem., Shanghai Inst. Org. Chem., Chin. Acad. Sci., Shanghai 200032, Peop. Rep.
China; Eng.) — Bartels
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