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1-(α-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α-Aminophosphonic Acids

  1. Kirill E. Metlushka1,2,
  2. Boris A. Kashemirov Dr.2,
  3. Viktor F. Zheltukhin Dr.1,
  4. Dilyara N. Sadkova1,
  5. Bernd Büchner Prof. Dr.3,
  6. Christian Hess Dr.3,
  7. Olga N. Kataeva Dr.1,3,
  8. Charles E. McKenna Prof. Dr.2,
  9. Vladimir A. Alfonsov Prof. Dr.1

Article first published online: 28 MAY 2009

DOI: 10.1002/chem.200802540

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 15, Issue 27, pages 6718–6722, July 6, 2009

Additional Information

How to Cite

Metlushka, Kirill E., Kashemirov, Boris A., Zheltukhin, Viktor F., Sadkova, Dilyara N., Büchner, B., Hess, C., Kataeva, Olga N., McKenna, Charles E. and Alfonsov, Vladimir A. (2009), 1-(α-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α-Aminophosphonic Acids. Chem. Eur. J., 15: 6718–6722. doi: 10.1002/chem.200802540

Author Information

  1. 1

    Kazan Scientific Center of the Russian Academy of Sciences, A. E. Arbuzov Institute of Organic and Physical Chemistry, Arbuzov str. 8, Kazan 420088 (Russia), Fax: (+7) 8432-75-5322

  2. 2

    Department of Chemistry, University of Southern California, Los Angeles, CA 90089-0744 (USA)

  3. 3

    IFW Dresden, Institute for Solid State Research, P.O. Box 270116, 01171 Dresden (Germany)

Publication History

  1. Issue published online: 29 JUN 2009
  2. Article first published online: 28 MAY 2009
  3. Manuscript Received: 4 DEC 2008

Funded by

  • Civilian Research and Development Foundation. Grant Number: RUC2-2638-KA-05
  • Russian Foundation for Basic Research. Grant Number: 07-03-00617

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Keywords:

  • aminophosphonic acids;
  • asymmetric synthesis;
  • Betti bases;
  • chiral auxiliaries;
  • imines

Abstract

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Ooh Betti! A new diastereoselective synthesis of α-aminophosphonates has been developed based on the reaction of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(α-aminobenzyl)-2-naphthol (Betti base; see scheme, X=H, CH3, or Br). The reaction proceeds with high diastereoselectivity. Treatment with HCl results in the formation of the desired α-aminophosphonic acids.

A new diastereoselective synthesis of α-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(α-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired α-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl.

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