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

The asymmetric 1,4-addition of Et 2 Zn 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 addi...

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Bibliographic Details
Published inRSC advances Vol. 6; no. 10; pp. 7755 - 7759
Main Authors Matsumoto, Keitaro, Nakano, Yuki, Shibata, Naoatsu, Sakaguchi, Satoshi
Format Journal Article
LanguageEnglish
Published 2016
Subjects
Asymmetry
Carbenes
Catalysis
Catalysts
Conjugates
Optical activity
Substrates
Switches
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Summary:The asymmetric 1,4-addition of Et 2 Zn 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.
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ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA25926F