Solvent-dependent strong asymmetric amplification in the catalytic enantioselective Henry reaction using the trans-N,N′-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine-CuCl2 complex

Koichi Tanaka; Tomoharu Iwashita; Erika Yoshida; Tomomi Ishikawa; Shinya Otuka; Zofia Urbanczyk-Lipkowska; Hiroki Takahashi

doi:10.1039/C5CC02302E

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Solvent-dependent strong asymmetric amplification in the catalytic enantioselective Henry reaction using the trans-N,N′-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine-CuCl₂ complex†

Koichi Tanaka,*^a Tomoharu Iwashita,^a Erika Yoshida,^a Tomomi Ishikawa,^a Shinya Otuka,^a Zofia Urbanczyk-Lipkowska^b and Hiroki Takahashi^c

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* Corresponding authors

^a Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan
E-mail: ktanaka@kansai-u.ac.jp
Fax: +81-06-6339-4026
Tel: +81-06-6368-0861

^b Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

^c Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan

Abstract

A strong asymmetric amplification was observed in the enantioselective Henry reaction catalyzed by the (R,R)-trans-N,N′-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine·CuCl₂ complex in AcOEt, while no amplification occurred in MeOH.

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Article information

DOI: https://doi.org/10.1039/C5CC02302E
Article type: Communication
Submitted: 19 Mar 2015
Accepted: 02 Apr 2015
First published: 02 Apr 2015

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Chem. Commun., 2015,51, 7907-7910

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Solvent-dependent strong asymmetric amplification in the catalytic enantioselective Henry reaction using the trans-N,N′-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine-CuCl₂ complex

K. Tanaka, T. Iwashita, E. Yoshida, T. Ishikawa, S. Otuka, Z. Urbanczyk-Lipkowska and H. Takahashi, Chem. Commun., 2015, 51, 7907 DOI: 10.1039/C5CC02302E

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Chemical Communications