Organic Letters 2007-09-13

N-(2-Nitrophenyl)proline: an intramolecular hydrogen bond forming reagent for the determination of the absolute configuration of primary amines.

Hee Choon Ahn, Kihang Choi

Index: Org. Lett. 9 , 3853, (2007)

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Abstract

N-(2-Nitrophenyl)proline (2-NPP) amides of primary amines have a conformational preference for intramolecular hydrogen bonding. Because of the strong and selective anisotropic effects on the amine substituents, the absolute configuration of alpha-chiral primary amines can be assigned by comparing the 1H chemical shifts of diastereomeric 2-NPP amides.