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Synlett 2009(19): 3167-3170  
DOI: 10.1055/s-0029-1218311
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Design and Synthesis of Chiral Imidazolidine-Pyridine Ligands

Takayoshi Arai*, Kuniko Suzuki
Graduate School of Science and Technology, Chiba University, Inage 263-8522, Japan
Fax: +81(43)2902889; e-Mail: tarai@faculty.chiba-u.jp;
Further Information

Publication History

Received 3 September 2009
Publication Date:
23 October 2009 (online)

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Abstract

Condensation of chiral diamines and aldehydes gave a series of chiral imidazolidine-pyridine compounds with high diastereoselectivities. The ability of these compounds to act as chiral ligands was examined in the catalytic Henry reaction.

Key words

asymmetric catalysis - ligands - imidazolidine - copper - Henry reaction

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11

Crystal Data
Orthorhombic, space group: P2 (1)2 (1)2 (1), a = 6.3601 (3), b = 8.1108 (4), c = 50.351 (3), V = 2597.4 (2), Z = 4, MoKα radiation, R 1 = 0.0456, wR 2 = 0.1458.

12

The MS value of m/z = 997.29 was also detected for [(L2b)2 - Cu]+. Although the mixing ratio of L2b and Cu(OAc)2 was reexamined to superior formation of the 1:1 complex, the ee of the Henry adduct was not improved.