Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

Gaku Fukuhara; Tomohiro Nakamura; Yuko Kawanami; Cheng Yang; Tadashi Mori; Hiroyuki Hiramatsu; Yasufumi Dan-oh; Kazuo Tsujimoto; Yoshihisa Inoue

doi:10.1039/C2CC34880B

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Chemical Communications

Issue 73, 2012

Urgent high quality communications from across the chemical sciences.

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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 Tsujimoto^b and Yoshihisa Inoue*^a

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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

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

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

DOI: 10.1039/C2CC34880B
Received 09 Jul 2012, Accepted 25 Jul 2012
First published online 25 Jul 2012

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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.

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Gaku Fukuhara
Tomohiro Nakamura
Yuko Kawanami
Cheng Yang
Tadashi Mori
Hiroyuki Hiramatsu
Yasufumi Dan-oh
Kazuo Tsujimoto
Yoshihisa Inoue

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Chemical Communications

Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

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Chemical Communications

Strictly diastereocontrolled photocyclodimerization of 2-anthracenecarboxylates tethered to cyclic tetrasaccharides

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