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

Research output: Contribution to journalArticle

20 Citations (Scopus)

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 α-chiral primary amines can be assigned by comparing the 1H chemical shifts of diastereomeric 2-NPP amides.

Original languageEnglish
Pages (from-to)3853-3855
Number of pages3
JournalOrganic Letters
Volume9
Issue number19
DOIs
Publication statusPublished - 2007 Sep 13

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Amines
reagents
Hydrogen
Hydrogen bonds
amines
hydrogen bonds
Amides
amides
configurations
Chemical shift
Hydrogen Bonding
chemical equilibrium
hydrogen
N-(2-Nitrophenyl)proline

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

N-(2-nitrophenyl)proline : An intramolecular hydrogen bond forming reagent for the determination of the absolute configuration of primary amines. / Ahn, Hee Choon; Choi, Kihang.

In: Organic Letters, Vol. 9, No. 19, 13.09.2007, p. 3853-3855.

Research output: Contribution to journalArticle

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