Issue 14, 2009
From the journal:

Chemical Communications

The first asymmetric Sonogashira coupling for the enantioselective generation of planar chirality in paracyclophanes†

Kazumasa Kanda,a   Tamami Koike,a   Kohei Endoa  and  Takanori Shibata*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, Japan
E-mail: tshibata@waseda.jp
Fax: +81 3-5286-8098
Tel: +81 3-5286-8098

Abstract

The double Sonogashira coupling of diiodoparacyclophanes with alkynes proceeded to give planarly chiral dialkynylparacyclophanes; a chiral Pd catalyst, which was prepared in situ from PdCl2(CH3CN)2 and Taniaphos, realized the first asymmetric Sonogashira coupling with up to ca. 80% ee.

Graphical abstract: The first asymmetric Sonogashira coupling for the enantioselective generation of planar chirality in paracyclophanes

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Article information

DOI
https://doi.org/10.1039/B818904H
Article type
Communication
Submitted
24 Oct 2008
Accepted
14 Jan 2009
First published
24 Feb 2009

Chem. Commun., 2009, 1870-1872

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The first asymmetric Sonogashira coupling for the enantioselective generation of planar chirality in paracyclophanes

K. Kanda, T. Koike, K. Endo and T. Shibata, Chem. Commun., 2009, 1870 DOI: 10.1039/B818904H

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