Ralf Haiges - Efforts towards cinchona alkaloid conformations and their catalytic functions in asymmetric synthesis: Exploitation 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, Shen,   Jingguo, Rahm, Martin, Ni, Chuanfa, Haiges, Ralf, Rasul, Golam,   Olah, George A., Abstracts of Papers, 243rd ACS National   Meeting & Exposition, San Diego, CA, United States, March   25-29, 2012, 2012, pp ORGN-524

      Abstract: Cinchona alkaloids and their derivs.   are widely utilized in asym. catalysis. Although close   conformation-catalytic activity relationships have been   established in several cinchona alkaloid-mediated catalytic   processes, conformational behavior of cinchona alkaloids is still   not fully understood. To address such an inherent problem, the   CF3 moiety has been incorporated as a conformational stabilizer   and a probe, which allows feasible conformational studies via 19F   NMR spectroscopy. Facilitated by this unique strategy, a wealth   of conformational information, otherwise inaccessible, has been   revealed. A further case study exploiting the CF3 probe has   manifested catalytically active conformations in the   enantioselective cyclopropanation of Ph vinyl ketone. [on   SciFinder(R)]

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