Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C2-symmetric chiral template

Mark M. Maturi; Gaku Fukuhara; Koichiro Tanaka; Yuko Kawanami; Tadashi Mori; Yoshihisa Inoue; Thorsten Bach

doi:10.1039/C5CC09107A

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Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C₂-symmetric chiral template†

Mark M. Maturi,^a Gaku Fukuhara,^b Koichiro Tanaka,^b Yuko Kawanami,^b Tadashi Mori,^b Yoshihisa Inoue*^b and Thorsten Bach*^a

Author affiliations

* Corresponding authors

^a Department Chemie and Catalysis Research Center (CRC), Technische Universität München, 85747 Garching, Germany
E-mail: thorsten.bach@ch.tum.de
Fax: +49 89 28913315
Tel: +49 89 28913330

^b Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan
E-mail: inoue@chem.eng.osaka-u.ac.jp
Fax: +81-6-6879-7923
Tel: +81-6-6879-7920

Abstract

A chiral template was constructed from 7-ethynyl-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one by Sonogashira cross-coupling with 4,4′′-diiodoterphenyl and was shown to bind the title compound strongly by hydrogen bonding resulting in enantioselectivities of up to 55% enantiomeric excess (ee) in the [4+4] anthracene photodimerization.

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Article information

DOI: https://doi.org/10.1039/C5CC09107A
Article type: Communication
Submitted: 03 Nov 2015
Accepted: 18 Nov 2015
First published: 18 Nov 2015
This article is Open Access

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Chem. Commun., 2016,52, 1032-1035

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Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C₂-symmetric chiral template

M. M. Maturi, G. Fukuhara, K. Tanaka, Y. Kawanami, T. Mori, Y. Inoue and T. Bach, Chem. Commun., 2016, 52, 1032 DOI: 10.1039/C5CC09107A

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