Enantioselective Fluorination of α-Substituted β-Diketones Using β,β-Diaryl Serines.

We report the enantioselective fluorination of α-substituted β-diketones using β,β-diaryl serines as a primary amine organocatalyst. The reaction affords the corresponding fluorinated products in yields of 74 to 99% with excellent enantioselectivity (75-95% ee ). Moreover, for synthetic applications, the diol, aldols, and the allylic fluoride were synthesized from 2a , maintaining excellent enantioselectivity (94% ee ). The control experiment reveals that the CO 2 H group of the β,β-diaryl serines plays an important role in inducing the high enantioselectivity.