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Russian Chemical Bulletin

, Volume 54, Issue 6, pp 1492–1495 | Cite as

New reaction pathway of dialkyl phosphorochloridites with salts of α-benzylideneaminocarboxylic acids. Direct synthesis of α-aminophosphonates from isostructural α-benzylideneaminocarboxylic acids

  • E. V. Bayandina
  • E. Yu. Davydova
  • M. A. Abaskalova
  • R. Z. Musin
  • V. A. Al'fonsov
Article

Abstract

The reaction of sodium N-benzylidenevalinate with dialkyl phosphorochloridites is accompanied by decarboxylation and yields diastereomeric N-(1-dialkoxyphosphoryl-2-methylpropyl)-N-(1-dialkoxyphosphorylbenzyl)amines.

Key words

α-benzylideneaminocarboxylic acids phosphorylation dialkyl phosphorochloridites α-aminophosphonates 

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References

  1. 1.
    Chemistry and Biochemistry of the Amino Acids, Ed. G. C. Barrett, Chapman and Hall, London—New York, 1985, 684 pp.Google Scholar
  2. 2.
    G. M. Coppola and H. F. Schuster, Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids, J. Wiley, New York, 1987, 416 pp.Google Scholar
  3. 3.
    V. P. Kukhar and H. R. Hudson, Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, J. Wiley and Sons, New York, 2000, 634 pp.Google Scholar
  4. 4.
    P. Kafarski and B. Lejczak, Phosphorus Sulfur, 1991, 63, 193.Google Scholar
  5. 5.
    O. I. Kolodiazhnyi, Tetrahedron Asimmetry, 1998, 9, 1279.Google Scholar
  6. 6.
    M. N. Dimukhametov, M. A. Abaskalova, E. Yu. Davydova, E. V. Bayandina, A. B. Dobrynin, I. A. Litvinov, and V. A. Alfonsov, Mendeleev Commun., 2004, 196.Google Scholar
  7. 7.
    V. A. Knizhnikov, O. P. Azizbekyan, and V. M. Prishchepenko, Zh. Obshch. Khim., 2003, 73, 1529 [Russ. J. Gen. Chem., 2003, 73 (Engl. Transl.)].Google Scholar
  8. 8.
    C. L. Hawkins and M. J. Davies, J. Chem. Soc., Perkin Trans., 1998, 2, 1937.Google Scholar
  9. 9.
    A. F. Al-Sayyab and A. Lawson, J. Chem. Soc. C, 1968, 406.Google Scholar
  10. 10.
    R. C. Corcoran and J. M. Green, Tetrahedron Lett., 1990, 31, 6827.Google Scholar
  11. 11.
    V. S. Brovarets, K. V. Zyuz', L. V. Budnik, V. A. Solodenko, and B. S. Drach, Zh. Obshch. Khim., 1993, 63, 1259 [Russ. J. Gen. Chem., 1993, 63 (Engl. Transl.)].Google Scholar
  12. 12.
    U. Schmidt, G. Oehme, and H. Krause, Synth. Commun., 1996, 26, 777.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • E. V. Bayandina
    • 1
  • E. Yu. Davydova
    • 1
  • M. A. Abaskalova
    • 1
  • R. Z. Musin
    • 1
  • V. A. Al'fonsov
    • 1
  1. 1.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research CenterRussian Academy of SciencesKazanRussian Federation

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