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In this work, a novel method for assigning the absolute configuration of a chiral primary amine has been developed based on the experimental and DFT-calculated  19 F NMR chemical shift differences of its derived two fluorinated amides by reacting with two enantiomers of a chiral derivatizing agent FPP (α-fluorinated phenylacetic phenylselenoester) separately. Comparing the experimental chemical shift difference    Δ    δ    α  -  F    R  ,  Sof (R)-FPA-amide/(S)-FPA-amide with the calculated Δδ α-F  R,S    of (R)-FPA-(R)-amide/(S)-FPA-(R)-amide, if the experimental Δδ α-F  R,S    has the same symbol (positive or negative) as one of the theoretical Δδ α-F  R,S   , the assigned configuration of the amine is considered to be consistent with the theoretical one. Our method could be applied to a broad substrate scope avoiding wrong conclusion due to empirical judgment.

Assigning the Absolute Configurations of Chiral Primary Amines Based on Experimental and DFT-Calculated 19F Nuclear Magnetic Resonance