Volume 45, Issue 28 pp. 4617-4619

Communication

The CFTA Method: A Reliable Procedure for the Determination of the Absolute Configuration of Chiral Primary Amines by ¹H NMR Spectroscopic Analysis^†

Yoshio Takeuchi Prof. Dr.,

Yoshio Takeuchi Prof. Dr.

[email protected]

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Masaru Segawa,

Masaru Segawa

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Hidehito Fujisawa,

Hidehito Fujisawa

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Kenji Omata Dr.,

Kenji Omata Dr.

Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

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Siegfried N. Lodwig Dr.,

Siegfried N. Lodwig Dr.

National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA

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Clifford J. Unkefer Dr.,

Clifford J. Unkefer Dr.

National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA

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Yoshio Takeuchi Prof. Dr.,

Yoshio Takeuchi Prof. Dr.

[email protected]

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Masaru Segawa,

Masaru Segawa

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Hidehito Fujisawa,

Hidehito Fujisawa

Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053

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Kenji Omata Dr.,

Kenji Omata Dr.

Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

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Siegfried N. Lodwig Dr.,

Siegfried N. Lodwig Dr.

National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA

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Clifford J. Unkefer Dr.,

Clifford J. Unkefer Dr.

National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA

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First published: 03 July 2006

https://doi.org/10.1002/anie.200600157

Citations: 29

^†

The authors are grateful to Dr. K. Kabuto of Tohoku University for his helpful suggestion. This work was partially supported by the National Stable Isotope Resource at Los Alamos (NIH 5P41 EB002166). CFTA=α-cyano-α-fluoro-p-tolylacetic acid.

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Graphical Abstract

Surprisingly stable anti-periplanar conformers of CFTA amides form the basis of a new and very reliable method for determining the absolute configuration of chiral primary amines by ¹H NMR spectroscopy (see picture). CFTA=α-cyano-α-fluoro-p-tolylacetic acid.

Supporting Information

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Volume45, Issue28

July 10, 2006

Pages 4617-4619

The CFTA Method: A Reliable Procedure for the Determination of the Absolute Configuration of Chiral Primary Amines by ¹H NMR Spectroscopic Analysis^†

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The CFTA Method: A Reliable Procedure for the Determination of the Absolute Configuration of Chiral Primary Amines by 1H NMR Spectroscopic Analysis†

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The CFTA Method: A Reliable Procedure for the Determination of the Absolute Configuration of Chiral Primary Amines by ¹H NMR Spectroscopic Analysis^†