Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Asymmetric Ring Opening of Terminal Epoxides Catalyzed by Chiral Co(III)-BF3 Salen Complex Immobilized on SBA-16

  • Published : 2009.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

The homogeneous B$F_3$ containing chiral Co(III) salen complexes were anchored non-covalently on the surfaces of mesoporous SBA-16 silica containing aluminum species. The Brönsted and Lewis acidic sites are attributed to the immobilization of fluorine functionalized chiral salen complexes on the supports. The FT-IR, UV, ESCA, and NMR analyses were performed to determine the structure of synthesized chiral salen catalysts. These heterogeneous catalysts could be applied in asymmetric ring opening of terminal epoxides by water and phenol derivatives. They showed very high enantioselectivity and yield more than 98% in the catalytic synthesis of optically active products.

Keywords

References

  1. Karlsson, A.; St$\ddot(o)$cker, M.; Schmidt, R. Micropor. Mesopor. Mater. 1999, 27, 181 https://doi.org/10.1016/S1387-1811(98)00252-2
  2. Demel, J.; Park, S.-E.; Cejka, J.; Stepnicka, P. Catal. Today 2008, 132, 63 https://doi.org/10.1016/j.cattod.2007.12.007
  3. Nur, H.; Hamid, H.; Endud, S.; Hamdan, H.; Ramli, Z. Mater. Chem. Phys. 2006, 96, 337 https://doi.org/10.1016/j.matchemphys.2005.07.023
  4. Kim, J. M.; Kwak, J. H.; Jun, S.; Ryoo, R. J. Phys. Chem. 1995, 99, 16742 https://doi.org/10.1021/j100045a039
  5. Groen, J. C.; Bach, T.; Ziese, U.; Paulaime-van Donk, A. M.; De Jong, K. P.; Moulijn, J. A.; Perez-Ramirez, J. J. Am. Chem. Soc. 2007, 127, 10792 https://doi.org/10.1021/ja052592x
  6. Cejka, J.; Mintova, S. J. Catal. Rev. 2008, 49, 457
  7. Yang, H.; Li, J.; Yang, J.; Liu, Z.; Yang, Q.; Li, C. Chem. Commun. 2007, 1086
  8. Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710 https://doi.org/10.1002/hlca.19960790621
  9. Vasylev, M. V.; Neumann, R. J. Am. Chem. Soc. 2004, 126, 126
  10. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936 https://doi.org/10.1126/science.277.5328.936
  11. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 307
  12. Thakur, S. S.; Chen, S.-W.; Li, W.; Shin, C.-K.; Kim, S.-J.; Koo, Y. M.; Kim, G.-J. J. Organomet. Chem. 2006, 691, 1862 https://doi.org/10.1016/j.jorganchem.2005.12.044
  13. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086 https://doi.org/10.1021/ja9910917
  14. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687 https://doi.org/10.1021/ja005867b
  15. Lee, K.-W.; Lee, C.-Y.; Kawthekar, R. B.; Kim, G.-J. Bull. Korean Chem. Soc. 2009, 30, 389 https://doi.org/10.5012/bkcs.2009.30.2.389
  16. Lee, K.-W.; Kawthekar, R. B.; Kim, G.-J. J. Korean Ind. Eng. Chem. 2007, 18, 330
  17. Greenwood, N. N.; Thomas, B. S. In Comprehensive Inorganic Chemistry (The Chemistry of Boron); Pergamon Press: Oxford, 1975; Chap. 11
  18. Yoon, S. B.; Sohn, K.; Kim, J. Y.; Shin, C.-H.; Hyeon, T. Adv. Mater. 2002, 14, 19 https://doi.org/10.1002/1521-4095(20020104)14:1<19::AID-ADMA19>3.0.CO;2-X
  19. Gan, J.; Wang, T.; Liu, Z.; Tan, W. Stud. Surf. Sci. Catal. 2007, 170B, 1567

Cited by

  1. Enantioselective Cobalt-Catalyzed Transformations vol.114, pp.5, 2014, https://doi.org/10.1021/cr4004055
  2. ChemInform Abstract: Asymmetric Ring Opening of Terminal Epoxides Catalyzed by Chiral Co(III)-BF3 Salen Complex Immobilized on SBA-16. vol.40, pp.51, 2009, https://doi.org/10.1002/chin.200951092
  3. Highly active oligomeric Co(salen) catalysts for the asymmetric synthesis of α-aryloxy or α-alkoxy alcohols via kinetic resolution of terminal epoxides vol.329, pp.1, 2010, https://doi.org/10.1016/j.molcata.2010.06.015
  4. Synthesis of carbon monolith with bimodal meso/macroscopic pore structure and its application in asymmetric catalysis vol.150, pp.1, 2009, https://doi.org/10.1016/j.cattod.2009.09.005
  5. Kinetic Evaluation of Cooperative [Co(salen)] Catalysts in the Hydrolytic Kinetic Resolution of rac-Epichlorohydrin vol.2, pp.10, 2009, https://doi.org/10.1002/cctc.201000162
  6. Synthesis of New Bimetallic Chiral Salen Catalyst Bearing Co(BF4)2 Salt and Its Application in Asymmetric Ring Opening of Epoxide vol.31, pp.10, 2009, https://doi.org/10.5012/bkcs.2010.31.10.2973
  7. Asymmetric Hydrolytic Kinetic Resolution with Recyclable Macrocyclic CoIII–Salen Complexes: A Practical Strategy in the Preparation of (R)‐Mexiletine and (S)‐Propranolol vol.18, pp.17, 2009, https://doi.org/10.1002/chem.201103574