Issue 47, 2009
From the journal:

Chemical Communications

A new approach to switching of enantioselectivity in NHC–Cu-catalyzed conjugate addition of alkylzincs to cyclic enones†

Masaki Okamoto,a   Yuko Yamamotoa  and  Satoshi Sakaguchi*a  

* Corresponding authors

a Department of Chemistry and Materials Engineering & High Technology Research Centre, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka, Japan
E-mail: satoshi@ipcku.kansai-u.ac.jp
Fax: +81-6-6339-4026
Tel: +81-6-6368-0867

Abstract

Conjugate addition of Et2Zn to 2-cyclohexen-1-one catalyzed by Cu(OTf)2 combined with an azolium salt derived from (S)-leucinol produced the corresponding (S)-adduct, while the use of Cu(acac)2 in combination with the same ligand afforded the (R)-adduct as a major product.

Graphical abstract: A new approach to switching of enantioselectivity in NHC–Cu-catalyzed conjugate addition of alkylzincs to cyclic enones

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Article information

DOI
https://doi.org/10.1039/B916103A
Article type
Communication
Submitted
05 Aug 2009
Accepted
13 Oct 2009
First published
04 Nov 2009

Chem. Commun., 2009, 7363-7365

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A new approach to switching of enantioselectivity in NHC–Cu-catalyzed conjugate addition of alkylzincs to cyclic enones

M. Okamoto, Y. Yamamoto and S. Sakaguchi, Chem. Commun., 2009, 7363 DOI: 10.1039/B916103A

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