Issue 11, 2005
From the journal:

Organic & Biomolecular Chemistry

Efficient axial chirality induction in biphenyldiol triggered by proton-transferred hydrogen bonding with chiral amine

Hideki Takagi,a   Tadashi Mizutani,*b   Takuya Horiguchi,c   Susumu Kitagawac  and  Hisanobu Ogoshic  

* Corresponding authors

a Graduate School of Science and Technology, Kobe University, Nada, Kobe, Japan

b Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto, Japan
E-mail: tmizutan@mail.doshisha.ac.jp
Fax: (81)774-65-6794
Tel: (81)774-65-6623

c Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan

Abstract

Axial chirality was induced in biphenyldiol upon binding chiral amines with the efficiency of chiral induction much improved at low temperature. At low temperatures, two molecules of amine were bound to biphenyldiol. The value of the dissymmetric g-factor increased as proton-transferred hydrogen bonds formed between biphenyldiol and amine. These results indicate that proton-transferred hydrogen bonding plays an important role in constructing a highly ordered chiral assembly.

Graphical abstract: Efficient axial chirality induction in biphenyldiol triggered by proton-transferred hydrogen bonding with chiral amine

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Article information

DOI
https://doi.org/10.1039/B419363F
Article type
Paper
Submitted
01 Jan 2005
Accepted
14 Mar 2005
First published
06 Apr 2005

Org. Biomol. Chem., 2005,3, 2091-2094

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Efficient axial chirality induction in biphenyldiol triggered by proton-transferred hydrogen bonding with chiral amine

H. Takagi, T. Mizutani, T. Horiguchi, S. Kitagawa and H. Ogoshi, Org. Biomol. Chem., 2005, 3, 2091 DOI: 10.1039/B419363F

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