Advertisement

Chemistry of Heterocyclic Compounds

, Volume 32, Issue 9, pp 1027–1034 | Cite as

Stereoselectivity in the reduction of chiral indoles to indolines

  • I. V. Trushkov
  • A. V. Karchava
  • M. A. Yarovskaya
Article
  • 39 Downloads

Abstract

The reduction of 2-alkylindoles containing a chiral substituent at the nitrogen atom by sodium cyanoborohydride in an acidic medium at -80°C is accompanied by the formation of indolines with S-configuration of the new chiral site at C(2). An AMI quantum chemical calculation showed that the major diastereomer has greater thermodynamic stability. However, the high diastereoselectivity of this reduction may be attributed only to the relative stability of the different conformations of the intermediate indoleninium cations leading to different diastereomers.

Keywords

Nitrogen Sodium Organic Chemistry Nitrogen Atom Indole 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. V. Kazchava, M. A. Yurovskaya, T. R. Wagner, B. L. Zybailov, and Yu. G. Bundel. Tetrahedron: Asymmetry,6 2895 (1995).Google Scholar
  2. 2.
    M. Nogrady, Stereoselective Synthesis [Russian translation], Mir, Moscow (1989), p. 56.Google Scholar
  3. 3.
    C. Hudlicky, Reductions in Organic Chemistry, Wiley, New York (1984).Google Scholar
  4. 4.
    R. A. More O'Ferrall, J. Chem. Soc., B, No. 2, 274(197O).Google Scholar
  5. 5.
    W. P. Jencks, Chem. Rev.,85, 511 (1985).Google Scholar
  6. 6.
    G. S. Hammond, J. Am. Chem. Soc.,77, 334 (1955).Google Scholar
  7. 7.
    E. R. Thornton, J. Am. Chem. Soc.,89, 2915 (1967).Google Scholar
  8. 8.
    G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, and J. L. Johnson, J. Am. Chem. Soc.,96, 7812 (1974).Google Scholar
  9. 9.
    J. I. Seemau, Chem. Rev.,83, 83 (1983)Google Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • I. V. Trushkov
  • A. V. Karchava
  • M. A. Yarovskaya

There are no affiliations available

Personalised recommendations