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.
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorMasaru Segawa
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorHidehito Fujisawa
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorKenji Omata Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan
Search for more papers by this authorSiegfried N. Lodwig Dr.
National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA
Search for more papers by this authorClifford J. Unkefer Dr.
National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA
Search for more papers by this authorYoshio Takeuchi Prof. Dr.
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorMasaru Segawa
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorHidehito Fujisawa
Faculty of Pharmaceutical Sciences, University of Toyama, Sugitani, Toyama 930-0194, Japan, Fax: (+81) 76-434-5053
Search for more papers by this authorKenji Omata Dr.
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan
Search for more papers by this authorSiegfried N. Lodwig Dr.
National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA
Search for more papers by this authorClifford J. Unkefer Dr.
National Stable Isotope Resource, Bioscience Division, MS E529, Los Alamos National Laboratory, Los Alamos, NM 87544, USA
Search for more papers by this authorThe 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.
Graphical Abstract
Überraschend stabile antiperiplanare Konformere von CFTA-Amiden bilden die Basis einer neuen und sehr zuverlässigen Methode, die absolute Konfiguration chiraler primärer Amine 1H-NMR-spektroskopisch zu bestimmen (siehe Bild). CFTA=α-Cyan-α-fluor-p-tolylessigsäure.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2006/z600157_s.pdf or from the author.
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- 14CCDC-291185 and CCDC-291186 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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