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Synlett 2005(17): 2670-2672  
DOI: 10.1055/s-2005-917101
LETTER
© Georg Thieme Verlag Stuttgart · New York

Design and Synthesis of a Chiral N-Tethered Bis(imidazoline) Ligand

Takayoshi Arai*a, Tomoe Mizukamia, Naota Yokoyamab, Daisuke Nakazatob, Akira Yanagisawaa
a Department of Chemistry, Faculty of Science, Chiba University, Inage 263-8522, Japan
Fax: +81(43)2902889; e-Mail: tarai@faculty.chiba-u.jp;
b Graduate School of Science and Technology, Chiba University, Inage 263-8522, Japan
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Publication History

Received 1 August 2005
Publication Date:
05 October 2005 (online)

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Abstract

A chiral nitrogen-tethered bis (imidazoline) ligand (Nb-imidazoline) was newly designed and synthesized in a divergent strategy. Thus, a single coupling reaction of primary amine with two molecules of chloromethylated imidazoline provided the Nb-imidazoline. The copper(II) triflate complex of Nb-imidazoline catalyzed a trans-selective cyclopropanation of styrene with ethyl di­azoacetate to give the adduct in high chemical yield with good enantiomeric excess up to 83%.

Key word

asymmetric catalysis - ligands - imidazoline - copper - ­cyclopropanation

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Nb-imidazoline is an abbreviation of N-tethered bis(imidazoline).