%0 Journal Article
%T Metal enolates of alpha-CF3 ketones: theoretical guideline, direct generation, and synthetic use.
%A Mikami K
%A Itoh Y
%J Chem Rec
%V 6
%N 1
%D 2006
%M 16470799
%F 6.935
%R 10.1002/tcr.20066
%X 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.