Advertisement

Russian Journal of Coordination Chemistry

, Volume 44, Issue 11, pp 688–692 | Cite as

Synthesis, Crystal Structure of Chiral Ferrocenyl Amino Alcohols, and Its Use for Asymmetric Transfer Hydrogenation

  • Y. M. Zhang
  • P. Q. Li
  • P. Liu
Article
  • 12 Downloads

Abstract

Two chiral ferrocenyl amino alcohols (IIIa and IIIb) have been synthesized for the iridium catalyzed asymmetric transfer hydrogenation of aromatic ketones. The structures of two chiral ferrocenyl amino alcohols have been determined by single crystal X-ray diffraction (CIF files CCDC nos. 1056737 (IIIa) and 1056734 (IIIb)). The results show that the activity and enantioselectivity of the chiral iridium catalyst are very sensitive to the substrate structure. Ir(I)-catalyzed asymmetric transfer hydrogenation of acetophenone resulted in moderate to good yield and lower enantioselectivity; asymmetric transfer hydrogenation of proopiophenone and 2-benzoylpyridine resulted in lower yield and lower enantioselectivity; as for 4-benzoylpyridine, good results have been achieved.

Keywords:

synthesis crystal structure chiral ferrocenyl amino alcohol asymmetric transfer hydrogenation chiral iridium complex 

Notes

ACKNOWLEDGMENTS

This work was supported by Natural Science Foundation of Hebei Province (no. B2014208094).

REFERENCES

  1. 1.
    Zhou, H., Zhang, L., Xu, C., and Luo, S., Ang. Chem. Int. Ed., 2015, vol. 54, no. 43, p. 12645.CrossRefGoogle Scholar
  2. 2.
    Pinaka, A., Dimotikali, D., Chankvetadze, B., et al., Synlett, 2013, vol. 24, no. 18, p. 2401.CrossRefGoogle Scholar
  3. 3.
    Aboulaala, K., Henry, C.G., Sinou, D., et al., J. Mol. Catal., A, 2005, vol. 237, p. 259.Google Scholar
  4. 4.
    Qiupeng Hu, Jianzhong Chen, Zhenfeng Zhang, et al., Org. Lett., 2016, vol. 18, no. 6, p. 1290.CrossRefGoogle Scholar
  5. 5.
    Blaser, H.-U., Adv. Synth. Catal., 2002, vol. 344, no. 1, p. 17.CrossRefGoogle Scholar
  6. 6.
    Tak, R., Kumar, M., Kureshy, R.I., et al., RSC Advances, 2016, vol. 6, no. 9, p. 7693.CrossRefGoogle Scholar
  7. 7.
    Arquarding, D.M., Klusacek, H., and Ugi, I., J. Am. Chem. Soc., 1970, vol. 92, p. 5389.CrossRefGoogle Scholar
  8. 8.
    Sheldrick, G.M., SHELXS-97, Program for X-ray Crystal Structure Solution, Göttingen: Univ. of Göttingen, 1997.Google Scholar
  9. 9.
    Sheldrick, G.M., SHELXL-97, Program for X-ray Crystal Structure Refinement, Göttingen: Univ. of Göttingen, 1997.Google Scholar
  10. 10.
    Guofu, Z.I. and Chenglie, Y.I.N., J. Mol. Catal. (China), 1997, vol. 11, no. 5, p. 359.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  1. 1.College of Sciences, Hebei University of Science & TechnologyShijiazhuangP.R. China

Personalised recommendations