Determination of the absolute configuration of primary amines in polar NMR solvents

被引：8
|
作者：
Ahn, Hee Choon
Choi, Kihang [1 ]
机构：
[1] Korea Univ, Dept Chem, Seoul 136701, South Korea
[2] Korea Univ, Ctr Electro & Photo Respons Mol, Seoul 136701, South Korea
来源：
CHEMISTRY LETTERS | 2007年 / 36卷 / 11期
关键词：
D O I：
10.1246/cl.2007.1330
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-(2-Nitrophenyl)proline (2-NPP) can be used in a wide range of solvents as an effective chiral auxiliary for the absolute configuration assignment of alpha-chiral primary amines. Even in competitive hydrogen-bonding solvents, 2-NPP amides of primary amines retain the conformation preference for intramolecular hydrogen bonding and produce significant anisotropic effects on the amine substituents. As a result, the absolute configuration can be assigned by comparing the H-1 NMR spectra of diastereomeric 2-NPP amides recorded in polar NMR solvents.
引用
收藏
页码：1330 / 1331
页数：2
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