A Chiral Lewis Acid with Two “Metal” Centers: Cooperative Binding of Two Amine Molecules to a Chiral Diboronic Ester

Authors

  • Dr. Kyoko Nozaki,

    1. Division of Material Chemistry, Graduate School of Engineering Kyoto University, Sakyo-ku, Kyoto, 606-01 (Japan) Telefax: Int. code + (75)761-8846
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  • Masanori Yoshida,

    1. Division of Material Chemistry, Graduate School of Engineering Kyoto University, Sakyo-ku, Kyoto, 606-01 (Japan) Telefax: Int. code + (75)761-8846
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  • Prof. Dr. Hidemasa Takaya

    Corresponding author
    1. Division of Material Chemistry, Graduate School of Engineering Kyoto University, Sakyo-ku, Kyoto, 606-01 (Japan) Telefax: Int. code + (75)761-8846
    • Division of Material Chemistry, Graduate School of Engineering Kyoto University, Sakyo-ku, Kyoto, 606-01 (Japan) Telefax: Int. code + (75)761-8846
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  • This work was supported by a Grant-in-Aid for Developmental Scientific Research (No. 06555272) and by a Grant-in-Aid for Scientific Research (No. 06750885; fellowship for K. N.) both from the Ministry of Education, Science and Culture, Japan. K. N. also thanks The Asahi Glass Foundation for partial financial support.

Abstract

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Lewis acid/Lewis base interactions and hydrogen bonds account for the cooperative binding of two molecules of benzylamine to the chiral diboronate 1. Exclusive formation of the 1:2 complex of the Lewis acid 1 and benzylamine is evident in the NMR spectrum, which implies that the binding of the first molecule provides a suitable binding site for the second amine molecule.

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