Skip to main content
SpringerLink
Log in

Preparation of S-Containing Aminophosphine and Phosphoramidite Ligands and Their Applications in Enantioselective C–C Bond Forming Reactions

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A series of phosphorus/sulfur ligands were readily prepared and successfully applied in the Pd-catalyzed enantioselective allylic substitution and Cu-catalyzed conjugated additions of cyclic enones, respectively. The Pd-catalyzed enantioselective allylic substitution showed the best yield of 98% with 74% ee. For the Cu-catalyzed conjugated additions of cyclic enones, the best yield of 100% with 76% ee at the temperature of −30 °C could be obtained.

Graphical Abstract

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

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Mellah M, Voituriez A, Schulz E (2007) Chem Rev 107:5133

    Article  CAS  Google Scholar 

  2. Pellissier H (2007) Tetrahedron 63:1297

    Article  CAS  Google Scholar 

  3. Masdeu-Bultó AM, Diéguez M, Martin E, Gómez M (2003) Coord Chem Rev 242:159

    Article  Google Scholar 

  4. Bayon JC, Claver C, Masdeu-Bulto AM (1999) Coord Chem Rev 73:193

    Google Scholar 

  5. Evans DA, Michael FE, Tedrow JS, Campos KR (2003) J Am Chem Soc 125:3534

    Article  CAS  Google Scholar 

  6. Ekegren JK, Roth P, Källstöm K, Tarnai T, Andersson PG (2003) Org Biomol Chem 1:358

    Article  CAS  Google Scholar 

  7. Faller JW, Wilt JC, Parr J (2004) Org Lett 6:1301

    Article  CAS  Google Scholar 

  8. Shi M, Wang CJ, Zhang W (2004) Chem Eur J 10:5507

    Article  CAS  Google Scholar 

  9. Mancheno OG, Arrayas RG, Carretero JC (2005) Organometallics 24:557

    Article  CAS  Google Scholar 

  10. Verdaguer X, Moyano A, Pericas MA, Riera A, Maestro MA, Mahia J (2000) J Am Chem Soc 122:10242

    Article  CAS  Google Scholar 

  11. Evans DA, Campos KR, Tedrow JS, Michael FE, Gagné MR (1999) J Org Chem 64:2994

    Article  CAS  Google Scholar 

  12. Evans DA, Campos KR, Tedrow JS, Michael FE, Gagné MR (2000) J Am Chem Soc 122:7905

    Article  CAS  Google Scholar 

  13. Hiroi K, Suzuki Y, Abe I (1999) Chem Lett 28:149

    Article  Google Scholar 

  14. Suzuki Y, Abe I, Hiroi K (1999) Heterocycles 50:89

    Article  CAS  Google Scholar 

  15. Hiroi K, Suzuki Y, Abe I, Kawagishi R (2000) Tetrahedron 56:4701

    Article  CAS  Google Scholar 

  16. Hiroi K, Izawa I, Takizawa T, Kawai K (2004) Tetrahedron 60:2155

    Article  CAS  Google Scholar 

  17. Enders D, Peters R, Runsink J, Bats JW (1999) Org Lett 1:1863

    Article  CAS  Google Scholar 

  18. Enders D, Peters R, Lochtman R, Raabe G, Runsink J, Bats JW (2000) Eur J Org Chem 2000:3399

    Article  Google Scholar 

  19. Tu T, Zhou YG, Hou XL, Dai LX, Dong XC, Yu YH, Sun J (2003) Organometallics 22:1255

    Article  CAS  Google Scholar 

  20. Priego J, Mancheno OG, Cabrera S, Arrayas RG, Llamas T, Carretero JC (2002) Chem Commun 2512

  21. Mancheno OG, Priego J, Cabrera S, Arrayas RG, Llamas T, Carretero JC (2003) J Org Chem 68:3679

    Article  Google Scholar 

  22. Routaboul L, Vincendeau S, Daran J-C, Manoury E (2005) Tetrahedron Asymmetry 16:2685

    Article  CAS  Google Scholar 

  23. Nakamura S, Fukuzumi T, Toru T (2004) Chirality 16:10

    Article  CAS  Google Scholar 

  24. She J, Ye L, Zhe J, Yuan Y (2007) Catal Lett 116:70

    Article  CAS  Google Scholar 

  25. Gladiali S, Medici S, Pirri G, Pulacchini S, Fabbri D (2001) Can J Chem 79:670

    Article  CAS  Google Scholar 

  26. Zhang W, Shi M (2004) Tetrahedron Asymmetry 15:3467

    Article  CAS  Google Scholar 

  27. Huang JD, Hu XP, Yu SB (2007) J Mol Catal A Chem 270:127

    Article  CAS  Google Scholar 

  28. Huang JD, Hu XP, Duan ZC (2006) Org Lett 8:4367

    Article  CAS  Google Scholar 

  29. Burns SA, Corriu RJP, Huynh V, Moreau JJE (1987) J Organomet Chem 333:281

    Article  CAS  Google Scholar 

  30. Lam FL, Au-Yeung TTL, Cheung HY, Kok SHL, Lam WS, Wong KY, Chan SC (2006) Tetrahedron Asymmetry 17:497

    Article  CAS  Google Scholar 

  31. Wang DY, Huang JD, Hu XP, Deng J, Yu SB, Duan ZC, Zheng Z (2008) J Org Chem 73:2011

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation (Changsha University of Science & Technology), and Changsha University of Science & Technology.

Author information

Authors and Affiliations

  1. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha, 410004, People’s Republic of China

    Ju-Lan Zeng, Zhong Cao & Dao-Wu Yang

  2. China Tobacco Hunan Industrial Corporation, Changsha, 410007, People’s Republic of China

    Sai-Bo Yu

Authors
  1. Ju-Lan Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sai-Bo Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhong Cao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dao-Wu Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Ju-Lan Zeng or Sai-Bo Yu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zeng, JL., Yu, SB., Cao, Z. et al. Preparation of S-Containing Aminophosphine and Phosphoramidite Ligands and Their Applications in Enantioselective C–C Bond Forming Reactions. Catal Lett 136, 243–248 (2010). https://doi.org/10.1007/s10562-010-0331-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0331-2

Keywords

Search

Navigation