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Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute (NRI), National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Umezono, Tsukuba, Ibaraki 305-8568, JapanReceived January 1, 2014, Accepted February 16, 2014Key Words : C-alkylation, Enolates, Fluoromethylation, O-alkylation, RegioselectivityKeto-enol interconversion is one of the most commonknown tautomerizations in carbonyl compounds, such as β-ketoesters. Due to the simultaneous exisitence of both keto-form and enol-form, carbonyl compounds generally ownambident reactivity on the carbon and oxygen sites. And thecontrol of C/O-regioselectivity in the alkylation of enolateshence became a historic research problem in organicchemistry.

Studies on the C/O-regioselectivity in Electrophilic Fluoromethylations of β-Ketoesters based on Thermodynamics by Ab initio Calculations