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J Org Chem. 2008 Sep 19;73(18):7357-60. doi: 10.1021/jo801205n. Epub 2008 Aug 8.

Stereoselective C9 carbon-carbon couplings of quinine: synthesis and conformational analysis of new C2-symmetric dimers.

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Department of Organic Chemistry and Institute of Physical and Theoretical Chemistry, Faculty of Chemistry, Wrocław University of Technology, 50-370 Wrocław, Poland.


An unexpected stereoselective direct dimerization occurred when 9-quinine halide was treated with butyllithium. The reaction of either (9S)- or (9R)-chloroquinine gave the same C2-symmetric dimer with 9R configuration (X-ray structure). A tentative mechanism involving radical recombination is discussed. This highly congested dimer forms two atropisomers, and their reversible interconversion was studied by NMR. Another C2-symmetric (9S)-quinine dimer connected solely by carbon-carbon bonds was obtained by the stereoselective coupling of bis(arylbromomagnesium) derivative with (9S)-chloroquinine.

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