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À propos de : Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New C2-Symmetric Dimers        

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  • Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New C2-Symmetric Dimers
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  • 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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