Skip to main content
SpringerLink
Log in

Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The preparation of new palladium complexes in situ that were composed of a series of chiral diphosphite ligands, which were derived from (1S,2S)-trans-1,2-cyclohexanediol, have been described. It was found that (1S,2S)-bis[(S)-1,1′-binaphthyl-2,2′-diyl]phosphite-cyclohexanediol was the suitable ligand in the Pd-catalyzed allylic alkylation, and up to 75% ee for (E)-dimethyl 2-(1,3-diphenylallyl)malonate was obtained. In compared with the results of the asymmetric allylic alkylation, (1S,2S)-bis[(R)-1,1′-binaphthyl-2,2′-diyl]phosphite-cyclohexanediol was proved to be the most efficient ligand in the Rh-catalyzed asymmetric hydrogenation of dimethyl itaconate and enamides with up to 99% ee. The stereochemically matched combinations between the diol skeleton and diaryl moieties of the ligands were essential for inducing high enantioselectivities in the two transformations. It was found that the sense of the enantiodiscrimination of the products was mainly determined by the configuration of the binaphthyl phosphite moieties.

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
Fig. 2

Similar content being viewed by others

References

  1. Diéguez M, Ruiz A, Muller G, Claver C, Jansat S, Gomez M (2001) Chem Commun 12:1132

    Article  Google Scholar 

  2. Fernandez-Perez H, Etayo P, Panossian A, Vidal-Ferran A (2011) Chem Rev 111:2119

    Article  CAS  Google Scholar 

  3. Dieguez M, Pamies O (2010) Acc Chem Res 43:312

    Article  CAS  Google Scholar 

  4. Falciola CA, Alexakis A (2008) Eur J Org Chem 2008:3765

    Article  Google Scholar 

  5. Jerphagnon T, Renaud J-L, Bruneau C (2004) Tetrahedron: Asymmetry 15:2101

    Article  CAS  Google Scholar 

  6. Lu Z, Ma S (2008) Angew Chem Int Ed 47:258

    Article  CAS  Google Scholar 

  7. Magre M, Mazuela J, Diéguez M, Pàmies O, Alexakis A (2012) Tetrahedron: Asymmetry 23:67

    Article  CAS  Google Scholar 

  8. Trost BM (2012) Org Process Res Dev 16:185

    Article  CAS  Google Scholar 

  9. Trost BM, Van Vranken DL (1996) Chem Rev 96:395

    Article  CAS  Google Scholar 

  10. Alegre S, Alberico E, Pàmies O, Diéguez M (2014) Tetrahedron: Asymmetry 25:258

    Article  CAS  Google Scholar 

  11. Diéguez M, Ruiz A, Claver C (2002) J Org Chem 67:3796

    Article  Google Scholar 

  12. Farkas G, Császár Z, Balogh S, Szöllősy Á, Gouygou M, Bakos J (2013) Catal Commun 36:94

    Article  CAS  Google Scholar 

  13. Panossian A, Fernández-Pérez H, Popa D, Vidal-Ferran A (2010) Tetrahedron: Asymmetry 21:2281

    Article  CAS  Google Scholar 

  14. Bravo MJ, Ceder RM, Grabulosa A, Muller G, Rocamora M, Bayón JC, Peral D (2015) Organometallics 34:3799

    Article  CAS  Google Scholar 

  15. Coll M, Pamies O, Dieguez M (2012) Dalton Trans 41:3038

    Article  CAS  Google Scholar 

  16. Gavrilov KN, Shiryaev AA, Zheglov SV, Bochelyuk MS, Chuchelkin IV, Tafeenko VA, Chernyshev VV, Zamilatskov IA, Mikhel IS (2015) Tetrahedron Lett 56:4756

    Article  CAS  Google Scholar 

  17. Kurihara K, Yamamoto Y, Miyaura N (2009) Tetrahedron Lett 50:3158

    Article  CAS  Google Scholar 

  18. Schmitz C, Leitner W, Franciò G (2015) Eur J Org Chem 2015:2889

    Article  CAS  Google Scholar 

  19. Shi WJ, Wang LX, Fu Y, Zhu SF, Zhou QL (2003) Tetrahedron: Asymmetry 14:3867

    Article  CAS  Google Scholar 

  20. Trost BM (1996) Acc Chem Res 29:355

    Article  CAS  Google Scholar 

  21. Wu X, Lin HC, Li ML, Li LL, Han ZY, Gong LZ (2015) J Am Chem Soc 137:13476

    Article  CAS  Google Scholar 

  22. Chen J, Lang F, Li D, Cun L, Zhu J, Deng J, Liao J (2009) Tetrahedron: Asymmetry 20:1953

    Article  CAS  Google Scholar 

  23. Cheung HY, Yu WY, Au-Yeung TTL, Zhou Z, Chan ASC (2009) Adv Synth Catal 351:1412

    Article  CAS  Google Scholar 

  24. Lam FL, Kwong FY, Chan AS (2010) Chem Commun 46:4649

    Article  CAS  Google Scholar 

  25. Benessere V, Lega M, Silipo A, Ruffo F (2011) Tetrahedron 67:4826

    Article  CAS  Google Scholar 

  26. Marinho VR, Rodrigues AI, Burke AJ (2008) Tetrahedron: Asymmetry 19:454

    Article  CAS  Google Scholar 

  27. Mikhel IS, Bernardinelli G, Alexakis A (2006) Inorg Chim Acta 359:1826

    Article  CAS  Google Scholar 

  28. Gual A, Castillon S, Pamies O, Dieguez M, Claver C (2011) Dalton Trans 40:2852

    Article  CAS  Google Scholar 

  29. Sanhes D, Gual A, Castillón S, Claver C, Gómez M, Teuma E (2009) Tetrahedron: Asymmetry 20:1009

    Article  CAS  Google Scholar 

  30. Swennenhuis BHG, Chen R, van Leeuwen PWNM, de Vries JG, Kamer PCJ (2009) Eur J Org Chem 2009:5796

    Article  Google Scholar 

  31. Pang ZB, Li HF, Tian M, Wang LL (2015) Tetrahedron: Asymmetry 26:1389

    Article  CAS  Google Scholar 

  32. Pang ZB, Li HF, Wang LL (2016) Chin Chem Lett 27:271

    Article  CAS  Google Scholar 

  33. Pang ZB, Xing AP, Wang LL (2015) Chem Res Chin Univ 31:756

    Article  CAS  Google Scholar 

  34. Xing AP, Bai CB, Wang LL (2013) Tetrahedron 69:455

    Article  CAS  Google Scholar 

  35. Zhao QL, Miao X, Wang LL (2013) Tetrahedron: Asymmetry 24:104

    Article  CAS  Google Scholar 

  36. Korostylev A, Tararov VI, Fischer C, Monsees A, Borner A (2004) J Org Chem 69:3220

    Article  CAS  Google Scholar 

  37. Clavero P, Grabulosa A, Rocamora M, Muller G, Font-Bardia M (2016) Eur J Inorg Chem 2016:4054

    Article  CAS  Google Scholar 

  38. Huang H, Liu X, Chen H, Zheng Z (2005) Tetrahedron: Asymmetry 16:693

    Article  CAS  Google Scholar 

  39. Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2003) Org Lett 5:4137

    Article  CAS  Google Scholar 

  40. Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2004) J Org Chem 69:2355

    Article  CAS  Google Scholar 

  41. Zhao Y, Huang H, Shao J, Xia C (2011) Tetrahedron: Asymmetry 22:769

    Article  Google Scholar 

Download references

Acknowledgements

The authors greatly appreciated the financial supports granted by the National Natural Science Foundation of China (Nos. 20773147, 21073211, and 21174155).

Author information

Authors and Affiliations

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, China

    Zengbo Pang, Mi Tian, Haifeng Li & Lailai Wang

  2. University of Chinese Academy of Sciences, Bejing, 100039, China

    Zengbo Pang & Mi Tian

Authors
  1. Zengbo Pang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mi Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Haifeng Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lailai Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lailai Wang.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 621 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pang, Z., Tian, M., Li, H. et al. Asymmetric Allylic Alkylation and Hydrogenation with Transition Metal Complexes of Diphosphite Ligands Based on (1S,2S)-Trans-1,2-cyclohexanediol. Catal Lett 147, 893–899 (2017). https://doi.org/10.1007/s10562-017-1986-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-017-1986-8

Keywords

Search

Navigation