Issue 10, 2016
From the journal:

RSC Advances

Enantioselectivity switch in copper-catalyzed conjugate addition reactions under the influence of a chiral N-heterocyclic carbene–silver complex†

Keitaro Matsumoto,a   Yuki Nakano,a   Naoatsu Shibataa  and  Satoshi Sakaguchi*a  

* Corresponding authors

a Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan
E-mail: satoshi@kansai-u.ac.jp

Abstract

The asymmetric 1,4-addition of Et2Zn to 2-cyclohexen-1-one using a Cu(I) salt/N-heterocyclic carbene (NHC)–Ag complex catalytic system afforded optically active 3-ethylcyclohexanone. The reversal of enantioselectivity using the same catalytic system was achieved by changing the order of the addition of substrates.

Graphical abstract: Enantioselectivity switch in copper-catalyzed conjugate addition reactions under the influence of a chiral N-heterocyclic carbene–silver complex

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Article information

DOI
https://doi.org/10.1039/C5RA25926F
Article type
Communication
Submitted
05 Dec 2015
Accepted
11 Jan 2016
First published
14 Jan 2016

RSC Adv., 2016,6, 7755-7759

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Enantioselectivity switch in copper-catalyzed conjugate addition reactions under the influence of a chiral N-heterocyclic carbene–silver complex

K. Matsumoto, Y. Nakano, N. Shibata and S. Sakaguchi, RSC Adv., 2016, 6, 7755 DOI: 10.1039/C5RA25926F

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