Ralf Haiges - Conformational Study of 9-Dehydro-9-Trifluoromethyl Cinchona Alkaloids via 19F NMR Spectroscopy: Emergence of Trifluoromethyl Moiety as a Conformational Stabilizer and a Probe.

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      Publication Details (including relevant citation   information): Prakash, G. K. Surya, Wang, Fang, Ni,   Chuanfa, Shen, Jingguo, Haiges, Ralf, Yudin, Andrei K., Mathew,   Thomas, Olah, George A., J. Am. Chem. Soc.,   2011, 133 (26), pp 9992-9995

      Abstract: The trifluoromethyl substituent has   been incorporated into quinidine as a conformational stabilizer   and a probe to provide straightforward insight into the   conformational behavior of cinchona alkaloids. By significantly   decreasing the rotation rate of the quinoline-carbinol bond, the   relatively bulky CF3 group enables the NMR signals of the syn and   anti conformers to be differentiated at room temp. In addn. to   the stabilizing effect, the introduction of the fluorinated   moiety also facilitates the application of 19F NMR spectroscopy,   thereby allowing conformational studies under various conditions   without the use of deuterated solvents. [on SciFinder(R)]

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