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Enantioselectivity switch in copper-catalyzed conjugate addition reactions under the influence of a chiral N-heterocyclic carbene–silver complex†
Keitaro Matsumoto,Yuki Nakano,Naoatsu Shibata,Satoshi Sakaguchi
RSC Advances Pub Date : 01/14/2016 00:00:00 , DOI:10.1039/C5RA25926F
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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