Issue 73, 2012
From the journal:

Chemical Communications

Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides†

Gaku Fukuhara,*a   Tomohiro Nakamura,a   Yuko Kawanami,a   Cheng Yang,a   Tadashi Mori,a   Hiroyuki Hiramatsu,b   Yasufumi Dan-oh,b   Kazuo Tsujimotob  and  Yoshihisa Inoue*a  

* Corresponding authors

a Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan
E-mail: gaku@chem.eng.osaka-u.ac.jp
Fax: +81 6 6879 7923
Tel: +81 6 6879 7922

b Hayashibara Co., Ltd., 1-1-3 Shimoishii, Kita-ku, Okayama 700-0907, Japan

Abstract

Photocyclodimerization of 2-anthracenecarboxylate tethered to a cyclic nigerosylnigerose scaffold gave a single chiral cyclodimer (out of two achiral and two chiral stereoisomers) in 99% optical and 96% chemical yields, achieving the ultimate stereocontrol of the supramolecular photochirogenesis in aqueous solution at 25 °C.

Graphical abstract: Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

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Article information

DOI
https://doi.org/10.1039/C2CC34880B
Article type
Communication
Submitted
09 jul 2012
Accepted
25 jul 2012
First published
25 jul 2012

Chem. Commun., 2012,48, 9156-9158

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Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

G. Fukuhara, T. Nakamura, Y. Kawanami, C. Yang, T. Mori, H. Hiramatsu, Y. Dan-oh, K. Tsujimoto and Y. Inoue, Chem. Commun., 2012, 48, 9156 DOI: 10.1039/C2CC34880B

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