Skip to main content
SpringerLink
Log in

Synthesis of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acids, intermediate products in the synthesis of cis-4-Aminochroman-3-ols

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Oxidation of accessible (R)-3-chloropropane-1,2-diol to (R)-3-chloro-2-hydroxypropanoic acid and subsequent reaction of the latter with ortho-substituted sodium phenoxide gave a number of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acid which are intermediate products in the synthesis of nonracemic 4-aminochroman-3-ols.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Davies, I.W., Taylor, M., Marcoux, J.-F., Matty, L., Wu, J., Hughes, D., and Reider, P.J., Tetrahedron Lett., 2000, vol. 41, p. 8021.

    Article  CAS  Google Scholar 

  2. Hansen, K.B., Rabbat, Ph., Springfield, Sh.A., Devine, P.N., Grabowski, E.J.J., and Reider, P.J., Tetrahedron Lett., 2001, vol. 42, p. 8743.

    Article  CAS  Google Scholar 

  3. The Merck Index, O’Neil, M.J., Ed., Whitehouse Station, NJ, USA: Merck and Co., 2006, 14th ed., 4945.

    Google Scholar 

  4. Ready, J.M. and Jacobsen, E.N., J. Am. Chem. Soc., 1999, vol. 121, p. 6086.

    Article  CAS  Google Scholar 

  5. Schaus, S.E., Brandes, B.D., Larrow, J.F., Tokunaga, M., Hansen, K.B., Gould, A.E., Furrow, M.E., and Jacobsen, E.N., J. Am. Chem. Soc., 2002, vol. 124, p. 1307.

    Article  CAS  Google Scholar 

  6. Hope, D.B. and Wälti, M., J. Chem. Soc. C, 1970, p. 2475.

    Google Scholar 

  7. Gerfaud, Th., Chiang, Y.-L., Kreituss, I., Russak, J.A., and Bode, J.W., Org. Proc. Res. Dev., 2012, vol. 16, p. 687.

    Article  CAS  Google Scholar 

  8. Wisniewski, K., Org. Prep. Proced. Int., 1999, vol. 31, p. 211.

    Article  CAS  Google Scholar 

  9. Bredikhin, A.A., Bredikhina, Z.A., and Zakharychev, D.V., Mendeleev Commun., 2012, vol. 22, p. 171.

    Article  CAS  Google Scholar 

  10. Loubinoux, B., Viriot-Chauveau, Ch., and Sinnes, J.L., Tetrahedron Lett., 1992, vol. 33, p. 2145.

    Article  CAS  Google Scholar 

  11. Riley, R.F., J. Am. Chem. Soc., 1950, vol. 72, p. 5712.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    Z. A. Bredikhina, A. V. Pashagin, A. V. Kurenkov & A. A. Bredikhin

Authors
  1. Z. A. Bredikhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Pashagin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kurenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Bredikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Z. A. Bredikhina.

Additional information

Original Russian Text © Z.A. Bredikhina, A.V. Pashagin, A.V. Kurenkov, A.A. Bredikhin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 546–550.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bredikhina, Z.A., Pashagin, A.V., Kurenkov, A.V. et al. Synthesis of enantiomerically pure 3-aryloxy-2-hydroxypropanoic acids, intermediate products in the synthesis of cis-4-Aminochroman-3-ols. Russ J Org Chem 50, 535–539 (2014). https://doi.org/10.1134/S1070428014040150

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014040150

Keywords

Search

Navigation