Skip to main content
SpringerLink
Log in

2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines in the reaction with chiral 2-arylpropionyl chloride predominantly yielded R*,R*-diastereomers. Ibuprofen acyl chloride as acylating agent was found to be more selective and sensitive to the changes in the reaction temperature as compared to naproxen acyl chloride and 2-phenylpropionyl chloride.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H. B. Kagan, J. C. Fiaud, Top. Stereochem., 1988, 18, 249.

    Article  CAS  Google Scholar 

  2. J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal., 2001, 343, 5.

    Article  CAS  Google Scholar 

  3. E. Vedejs, M. Jure, Angew. Chem., Int. Ed., 2005, 44, 3974.

    Article  CAS  Google Scholar 

  4. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem., Int. Ed., 2004, 43, 788.

    Article  CAS  Google Scholar 

  5. F. van Rantwijk, R. A. Sheldon, Tetrahedron, 2004, 60, 501.

    Article  Google Scholar 

  6. K. Ditrich, Synthesis, 2008, 2283.

  7. S. Takayama, S. T. Lee, S.-C. Hung, C.-H. Wong, Chem. Commun., 1999, 127.

  8. M. Nechab, N. Azzi, N. Vanthuyne, J. Org. Chem., 2007, 72, 6918.

    Article  CAS  Google Scholar 

  9. S. Arai, S. Bellemin-Lapponnaz, G. Fu, Angew. Chem., Int. Ed., 2001, 40, 234.

    Article  CAS  Google Scholar 

  10. F. Arp, G. Fu, J. Am. Chem. Soc., 2006, 128, 14264.

    Article  CAS  Google Scholar 

  11. K. Arnold, B. Davies, D. Hérault, A. Whiting, Angew. Chem., Int. Ed., 2008, 47, 2673.

    Article  CAS  Google Scholar 

  12. C. K. De, E. G. Klauber, D. Seidel, J. Am. Chem. Soc., 2009, 131, 17060.

    Article  CAS  Google Scholar 

  13. B. Fowler, P. J. Mikochik, S. J. Miller, J. Am. Chem. Soc., 2010, 132, 2870.

    Article  CAS  Google Scholar 

  14. K. Kondo, T. Kurosaki, Y. Murakami, Synlett, 1998, 725.

  15. N. Maezaki, A. Furusawa, S. Uchida, T. Tanaka, Tetrahedron, 2001, 57, 9309.

    Article  CAS  Google Scholar 

  16. A. Karnik, S. Kamath, Tetrahedron: Asymmetry, 2008, 19, 45.

    Article  CAS  Google Scholar 

  17. S. Arseniyadis, A. Valleix, A. Wagner, C. Mioskowski, Angew. Chem., Int. Ed., 2004, 43, 3314.

    Article  Google Scholar 

  18. A. G. Al-Sehemi, R. S. Atkinson, J. Fawcett, J. Chem. Soc., Perkin Trans. 1, 2002, 257.

  19. Z. J. Kamiński, B. Kolesińska, J. E. Kamińska, J. Góra, J. Org. Chem., 2001, 66, 6276.

    Article  Google Scholar 

  20. V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Korolyova, M. I. Kodess, O. N. Chupakhin, M. H. Kim, H. S. Lee, Y. J. Park, K.-Ch. Kim, Tetrahedron: Asymmetry, 1999, 10, 2691.

    Article  CAS  Google Scholar 

  21. V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. I. Grishakov, V. N. Charushin, O. N. Chupakhin, Mendeleev Commun., 2002, 12, 27.

    Article  Google Scholar 

  22. V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Korolyova, M. I. Kodess, V. N. Charushin, O. N. Chupakhin, Tetrahedron: Asymmetry, 2003, 14, 1985.

    Article  CAS  Google Scholar 

  23. V. P. Krasnov, G. L. Levit, M. I. Kodess, V. N. Charushin, O. N. Chupakhin, Tetrahedron: Asymmetry, 2004, 15, 859.

    Article  CAS  Google Scholar 

  24. V. P. Krasnov, G. L. Levit, M. A. Koroleva, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 2004, 1203 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1253].

  25. D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin, Tetrahedron: Asymmetry, 2010, 21, 936.

    Article  CAS  Google Scholar 

  26. H. Herlinger, H. Kleimann, I. Ugi, Liebigs Ann. Chem., 1967, 706, 37.

    Article  CAS  Google Scholar 

  27. L. Leclerq, I. Suisse, F. Agbossou-Niedercorn, Eur. J. Org. Chem., 2010, 2696.

  28. I. Shiina, K. Nakata, K. Ono, Y. Onda, M. Itagak, J. Am. Chem. Soc., 2010, 132, 11629.

    Article  CAS  Google Scholar 

  29. A. Andreou, N. Al Shaye, H. Brown, J. Eames, Tetrahedron Lett., 2010, 51, 6935.

    Article  CAS  Google Scholar 

  30. JP Pat. 2000178265; Chem. Abstrs, 2000, 133, 43530.

    Google Scholar 

  31. A. Horeau, Tetrahedron, 1975, 31, 1307.

    Article  CAS  Google Scholar 

  32. I. Hayakawa, S. Atarashi, S. Yokohama, M. Imamura, K.-I. Sakano, M. Furukawa, Antimicrob. Agents Chemother., 1986, 29, 163.

    CAS  Google Scholar 

  33. T. Manimaran, G. P. Stahly, Tetrahedron: Asymmetry, 1993, 4, 1949.

    Article  CAS  Google Scholar 

  34. E. J. Ebbers, G. J. Ariaans, A. Bruggink, B. Zwanenburg, Tetrahedron: Asymmetry, 1999, 10, 3701.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    E. N. Chulakov, D. A. Gruzdev, G. L. Levit, L. Sh. Sadretdinova, V. P. Krasnov & V. N. Charushin

Authors
  1. E. N. Chulakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. A. Gruzdev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. L. Levit
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. Sh. Sadretdinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. P. Krasnov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Krasnov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 926–931, May, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chulakov, E.N., Gruzdev, D.A., Levit, G.L. et al. 2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines. Russ Chem Bull 60, 948–954 (2011). https://doi.org/10.1007/s11172-011-0149-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0149-0

Key words

Search

Navigation