An NMR method for determination of configuration of β-substituted carboxylic acids

Thomas R. Hoye; Abdel Sattar S. Hamad; Dmitry O. Koltun; Manomi A. Tennakoon

doi:10.1016/S0040-4039(00)00163-5

An NMR method for determination of configuration of β-substituted carboxylic acids

Thomas R. Hoye, Abdel Sattar S. Hamad, Dmitry O. Koltun, Manomi A. Tennakoon

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

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Abstract

The absolute configuration of the stereogenic center at the β-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH₂ or 1-NpCH(Me)NH₂]. Acids of known configuration and with a variety of β-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration.

Original language	English (US)
Pages (from-to)	2289-2293
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)00163-5
State	Published - Apr 1 2000

Bibliographical note

Funding Information:
This work was supported in part by the National Institutes of Health and an Egyptian Ministry of Education Fellowship (to A.-S.S.H.). We thank Drs. Maren Pink and Victor J. Young of the University of Minnesota X-ray Crystallographic Laboratory for determination of the structure of syn- vi .

Keywords

Carboxylic acids
Configuration
NMR spectroscopy
Stereochemistry

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10.1016/S0040-4039(00)00163-5

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AU - Hamad, Abdel Sattar S.

AU - Koltun, Dmitry O.

AU - Tennakoon, Manomi A.

N1 - Funding Information: This work was supported in part by the National Institutes of Health and an Egyptian Ministry of Education Fellowship (to A.-S.S.H.). We thank Drs. Maren Pink and Victor J. Young of the University of Minnesota X-ray Crystallographic Laboratory for determination of the structure of syn- vi .

PY - 2000/4/1

Y1 - 2000/4/1

N2 - The absolute configuration of the stereogenic center at the β-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of β-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration.

AB - The absolute configuration of the stereogenic center at the β-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of β-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration.

KW - Carboxylic acids

KW - Configuration

KW - NMR spectroscopy

KW - Stereochemistry

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An NMR method for determination of configuration of β-substituted carboxylic acids

Abstract

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