Skip to main content
Log in

Two approaches to the synthesis of planar chiral quinolinyl cymantrene

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

Abstract

Two approaches to the synthesis of planar chiral (SMn,S)-[2-(quinolin-2-yl)cymantren-1-yl]-p-tolylsulfoxide have been developed. One of them is based on the Negishi cross-coupling reaction, while other one is based on the SNH cross-coupling.

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

Access this article

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. Ferrocenes: Homogeneous Catalysis, Eds A. Togni, T. Hayashi, VCH Weinheim, Germany, 1995, p. 531.

    Google Scholar 

  2. I. A. Utepova, O. N. Chupakhin, V. N. Charushin, Hetero-cycles, 2008, 76, 39.

    Article  CAS  Google Scholar 

  3. O. Delacroix, J. A. Gladysz, Chem. Commun., 2003, 665.

    Google Scholar 

  4. H. Hu, W.-Y. Wu, T. Takahashi, K. Yoshida, M. Ogasawara, Eur. J. Inorg. Chem., 2017, 2, 325.

    Article  Google Scholar 

  5. J. H. Lee, S. U. Son, Y. K. Chung, Tetrahedron Asymmetry, 2003, 14, 2109.

    Article  CAS  Google Scholar 

  6. N. M. Loim, M. A. Kondratenko, V. I. Sokolov, J. Org. Chem., 1994, 59, 7485.

    Article  CAS  Google Scholar 

  7. M. Ogasawara, Y.-Y. Tseng, Q. Liu, N. Chang, X. Yang, T. Takahashi, K. Kamikawa, Organometallics, 2017, 7, 1430.

    Article  Google Scholar 

  8. W.-P. Deng, V. Snieckus, C. Metallinos, in Chiral Ferrocenes in Asymmetric Catalysis, Eds L.-X. Dai, X.-L. Hou, Wiley-VCH, Weinheim, 2010, p. 15.

  9. Chiral Ferrocenes in Asymmetric Catalysis, Eds L.-X. Dai, X.-L. Hou, Wiley-VCH, Weinheim, Germany, 2010, p. 414.

    Google Scholar 

  10. B. Ferbera, H. B. Kagan, Adv. Synth. Catal., 2007, 349, 493.

    Article  Google Scholar 

  11. Z. S. Han, A. M. Meyer, Y. Xu, Y. Zhang, R. Busch, S. Shen, N. Grinberg, B. Z. Lu, D. Krishnamurthy, C. H. Senanayake, J. Org. Chem., 2011, 76, 5480.

    Article  CAS  Google Scholar 

  12. O. N. Chupakhin, I. A. Utepova, I. S. Kovalev, V. L. Rusinov, Z. A. Starikova, Eur. J. Org. Chem., 2007, 5, 857.

    Article  Google Scholar 

  13. I. A. Utepova, A. A. Musikhina, O. N. Chupakhin, P. A. Slepukhin, Organometallics, 2011, 30, 3047.

    Article  CAS  Google Scholar 

  14. A. A. Musikhina, I. A. Utepova, P. O. Serebrennikova, O. N. Chupakhin, V. N. Charushin, Russ. J. Org. Chem., 2013, 49, 1191.

    Article  CAS  Google Scholar 

  15. I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A. Musikhina, V. N. Charushin, J. Org. Chem., 2014, 79, 8659.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to O. N. Chupakhin.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 20-43-660054) and by the Ministry of Education and Science of the Russian Federation (State Task No. 0836-2020-0058).

Based on the materials of the 4th Russian Conference on Medicinal Chemistry with international participation (June 9–14, 2019, Ekaterinburg, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0458–0460, March, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chupakhin, O.N., Serebrennikova, P.O., Utepova, I.A. et al. Two approaches to the synthesis of planar chiral quinolinyl cymantrene. Russ Chem Bull 69, 458–460 (2020). https://doi.org/10.1007/s11172-020-2784-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2784-9

Keywords

Navigation