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Metal enolates of alpha-CF3 ketones: theoretical guideline, direct generation, and synthetic use
Authors:Mikami Koichi  Itoh Yoshimitsu
Institution:Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552. kmikami@o.cc.titech.ac.jp
Abstract:The difficulty as well as the significance of the direct generation of metal enolates of alpha-CF(3) ketones cannot be easily understood by chemists unfamiliar with F. In sharp contrast to the sunny side of non-F, hydrocarbon chemistry, F chemistry has long been overshadowed. Metal enolates of carbonyl compounds are synthetically important in C-C bond-forming reactions. However, the metal enolates of fluorinated carbonyl compounds have been severely limited to alpha-F metal enolates. Alpha-CF(3) metal enolates have generally been recognized as unstable and difficult to prepare because of the facile beta-M-F elimination. However, we have developed a direct generation and synthetic application of alpha-CF(3) metal enolates. Therefore, the present results regarding the direct generation and synthetic use of metal enolates of alpha-CF(3) ketones might be recognized as a real breakthrough for the general use of metal enolates in F chemistry.
Keywords:enolate  diastereoselectivity  density functional calculation  trifluoromethylation
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