Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Osmylated Macroporous Cinchona Alkaloid Resins: Highly Efficient and Recyclable Catalysts for Asymmetric Dihydroxylation of Olefins

  • Published : 2004.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

A simple method for simultaneous recovery and reuse of $OsO_4$ and alkaloid ligand in the asymmetric dihydroxylation of olefins has been developed by using macroporous alkaloid resins bearing residual vinyl groups.

Keywords

References

  1. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. https://doi.org/10.1021/cr00032a009
  2. Beller, M.; Sharpless, K. B. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; VCH: 1996; Vol. 2, pp 1009-1024.
  3. Marko, I. E.; Svendsen, J. S. Dihydroxylation of Carbon-Carbon Double Bonds in Comprehensive Asymmetric Catalysis II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer Verlag: Berlin, 1999; Vol. 2, pp 713-787.
  4. Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation-Discovery and Development in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: 2000; pp 357-398.
  5. Bolm, C.; Hildebrand, J. P.; Muniz, K. Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: 2000; pp 399-428.
  6. Song, C. E.; Lee, S.-g. Chem. Rev. 2002, 102, 3495-3524. https://doi.org/10.1021/cr0103625
  7. Salvadori, P.; Pini, D.; Petri, A.; Mandoli, A. In Chiral Catalyst Immobilization and Recycling; De Vos, D. E. Vankelecom, I. F. J. Jacobs, P. A., Eds.; Wiley-VCH: 2000; pp 235-246.
  8. Salvadori, P.; Pini, D.; Petri, A. Synlett 1999, 1181-1190.
  9. Bolm, C.; Gerlach, A. Eur. J. Org. Chem. 1998, 21-27.
  10. Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094-6095. https://doi.org/10.1021/jo981127y
  11. Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229-11230. https://doi.org/10.1021/ja993099m
  12. Kobayashi, S.; Ishida, T.; Akiyama, R. Org. Lett. 2001, 3, 2649-2652. https://doi.org/10.1021/ol0161965
  13. Choudary, B. M.; Chowdari, N. S.; Kantam, M. L.; Raghavan, K. V. J. Am. Chem. Soc. 2001, 123, 9220-9221. https://doi.org/10.1021/ja016101u
  14. Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Kantam, M. L. J. Am. Chem. Soc. 2002, 124, 5341-5349. https://doi.org/10.1021/ja017889j
  15. Yang, J. W.; Han, H.; Roh, E. J.; Lee, S.-g.; Song, C. E. Org. Lett. 2002, 4, 4685 https://doi.org/10.1021/ol027109r
  16. Jo, C. H.; Han, S.-H.; Yang, J. W.; Roh, E. J.; Shin, U.-S.; Song, C. E. Chem. Commun. 2003, 1312-1313.
  17. Song, C. E.; Yang, J. W.; Ha, H. J.; Lee, S.-g. Tetrahedron: Asymmetry 1996, 7, 645-648. https://doi.org/10.1016/0957-4166(96)00054-7
  18. Kwong, H.-L.; Sorato, C.; Ogino, Y.; Chen, H.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 2999. https://doi.org/10.1016/S0040-4039(00)89008-5
  19. Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766-768. https://doi.org/10.1021/jo00289a066

Cited by

  1. Nontoxic, nonvolatile, and highly efficient osmium catalysts for asymmetric dihydroxylation of alkenes and application to one mol-scale synthesis of an anticancer drug, camptothecin intermediate vol.2, pp.19, 2012, https://doi.org/10.1039/c2ra21123h
  2. Dimeric Cinchona alkaloids vol.19, pp.2, 2015, https://doi.org/10.1007/s11030-014-9563-1
  3. Osmylated Macroporous Cinchona Alkaloid Resins: Highly Efficient and Recyclable Catalysts for Asymmetric Dihydroxylation of Olefins. vol.36, pp.13, 2005, https://doi.org/10.1002/chin.200513073
  4. New Mono-Quarternized Bis-Cinchona Alkaloid Ligands for Asymmetric Dihydroxylation of Olefins in Aqueous Medium: Unprecedented High Enantioselectivity and Recyclability vol.348, pp.18, 2006, https://doi.org/10.1002/adsc.200600253
  5. Osmium Tetroxide-(QN)2PHAL-Sugar: a New Recyclable Catalyst System for Asymmetric Dihydroxylation of Olefins vol.26, pp.11, 2004, https://doi.org/10.5012/bkcs.2005.26.11.1839