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

doi:10.1021/ol7017455

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

21 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 language	English
Pages (from-to)	3853-3855
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	19
DOIs	https://doi.org/10.1021/ol7017455
Publication status	Published - 2007 Sept 13

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol7017455

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title = "N-(2-nitrophenyl)proline: An intramolecular hydrogen bond forming reagent for the determination of the absolute configuration of primary amines",

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.",

author = "Ahn, {Hee Choon} and Kihang Choi",

year = "2007",

month = sep,

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doi = "10.1021/ol7017455",

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journal = "Organic Letters",

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AU - Ahn, Hee Choon

AU - Choi, Kihang

PY - 2007/9/13

Y1 - 2007/9/13

N2 - 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.

AB - 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.

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U2 - 10.1021/ol7017455

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M3 - Article

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JF - Organic Letters

IS - 19

ER -

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

Abstract

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