Abstract
The regioselectivity of the Baeyer-Villiger reaction of alpha-CF(3)-ketone is completely reversed from that in alpha-F(eq)-ketone. Theoretical study rationalized that the reaction proceeds with the sterically demanding CF(3) group in an axial orientation by strong dipole interaction. The guiding principle that strong dipole interaction can overcome steric repulsion as a determining factor not only in regio- but also in stereocontrol is proposed. [reaction: see text]
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