Cinchona alkaloid�primary amines have been shown previously to catalyze the a-fluorination of cyclic ketones in high yields and with high enantioselectivity. Here, by quantum chemical computations, we show that a conformationally well-defined partial seven-membered ring formed from the substrate and the organocatalyst during fluorine transfer explains the sense and level of enantiocontrol.

Enantioselective fluorination of ketones organocatalyzed by cinchona alkaloid-derived primary amines: A stereoselectivity model

247th National Meeting (2014)

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