Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Application of Chiral Ligands Heterogenized over Solid Supports on Enantioselective Catalysis

고체 담체에 고정화된 키랄리간드의 비대칭 촉매반응에의 응용

  • Lee, Kwang-Yeon (Department of Chemical Engineering, Inha university) ;
  • Kawthekar, Rahul B. (Department of Chemical Engineering, Inha university) ;
  • Kim, Geon-Joong (Department of Chemical Engineering, Inha university)
  • 이광연 (인하대학교 생명화학공학부) ;
  • 카테카 라울 (인하대학교 생명화학공학부) ;
  • 김건중 (인하대학교 생명화학공학부)
  • Received : 2006.11.24
  • Published : 2006.12.10
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Abstract

The trend towards the application of single enantiomers of chiral compounds is undoubtedly increasing. Among the various methods to obtain one single enantio-riched compound selectively, enantioselective catalysis is the most attractive method. Especially, it is important to increase the activity, selectivity and lifetime of usually expensive chiral catalysts with a minute quantity in the enantioselective synthesis. Immobilization of active homogeneous catalysts is a fashionable topic in asymmetric catalysis, providing the inherent advantage of easy separation and better handling properties. Many different ways have been investigated to improve the enantioselectivity of products and to recycle the catalysts. This review mainly focused on the present scope and limitations of different types of enantioselective heterogeneous catalysts.

광학순도가 높은 이성체의 응용은 최근 들어 크게 증가되고 있는 추세이다. 여러 가지 방법 중에서도 비대칭 촉매합성반응을 통하여 선택적으로 순수한 광학이성체를 합성하는 것이 가장 매력적인 방법이다. 특히 키랄화합물을 합성하는 비대칭촉매반응에 있어서는 가격이 비싼 촉매를 소량 사용하면서도 활성이나 광학선택성 및 촉매수명을 높이도록 하는 조건이 매우 중요하게 대두된다. 활성이 큰 키랄촉매를 고정화시키면 반응 후에 반응혼합물을 여과법으로 쉽게 제거할 수 있다는 등의 취급상 용이한 점을 제공한다. 키랄촉매반응에서 생성물의 광학선택성을 향상시키고 여러 번 촉매를 재사용할 수 있도록 하려는 다양한 방법이 연구되고 있다. 본 총설에서는 여러 종류의 광학선택적인 불균일촉매에 관한 연구의 현황과 제한점 등을 주로 다루었다.

Keywords

Acknowledgement

Supported by : Inha University

References

  1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiely, New York (1994)
  2. R. A. Sheldon, Chirotechnology; Industrial Synthesis of Optical Active Compounds, Marcel Dekker, New York (1994)
  3. (a) H.-U. Blaser, B. Pugin, and M. Studer, Chiral Catalyst Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom and P. A. Jacobs, WILEY-VCH, chap 1,2 (1998). (b) A. Tai and T. Sugimura, WILEY-VCH, chap 8, 173 (1998)
  4. H. U. Blaser and H. P. J. Wiehl, J. Mol. Cat., 215 (1991)
  5. B. Minder, M. Schurch, T. Mallat, A. Baiker, T. Heinz, and A. Pfaltz, J. Catal., 160, 261 (1996) https://doi.org/10.1006/jcat.1996.0144
  6. B. Minder, T. Mallat, A. Baiker, G. Wang, T. Heinz, and A. Pfaltz, J. Catal., 154, 371 (1995) https://doi.org/10.1006/jcat.1995.1179
  7. H.-U. Blaser and B. Pugin, Chiral Reactions in Heterogeneous Catalysis, ed. G. Jannes and V. Dubois, Plenum Press, 33 (1995)
  8. S. Bhaduri, V. S. Darshane, K. Sharma, and D. Mukesh, J. Chem. Soc. Chem. Commun., 1738 (1992)
  9. R. L. Augustin, Heterogeneous Catalysis for the Synthetic Chemist, ed. Marcell Dekker, 313 (1996)
  10. K. Balazsik, B. Torok, G. Szakonyi, and M. Bartok, Applied Catalysis A: General, 182, 53 (1999) https://doi.org/10.1016/S0926-860X(98)00419-0
  11. A. Corma, M. Iglesias, C. del Pino, and F. Sanchez, J. Chem. Soc., Chem. Commun., 1253 (1991)
  12. U. Nagel and E. Kinzel, J. Chem. Soc. Chem. Commun., 1098 (1986)
  13. D. S. Shephard, Stud. Surf. Sci. Catal., 129, 797 (2000)
  14. D. Pini, A. Mandoli, S. Orlandi, and P. Salvadori, Tetrahedron: Asymmetry, 10, 3883 (1999) https://doi.org/10.1016/S0957-4166(99)00426-7
  15. G.-J. Kim and J.-H. Shin, Tetrahedron Letters, 40, 6827 (1999) https://doi.org/10.1016/S0040-4039(99)01407-0
  16. D. C. Sherrington, Catalysis Today, 57, 87 (2000) https://doi.org/10.1016/S0920-5861(99)00311-9
  17. L. Canali, E. Cowan, H. Deleuze, C. L. Gibson, and D. C. Sherrington, Chem. Commun., 23, 2561 (1998)
  18. D. Brunel, P. Sutra, and F. Fajula, Stud. Surf. Sci. Catal., 129, 773 (2000) https://doi.org/10.1016/S0167-2991(00)80282-7
  19. S. Xiang, Y. Zhang, Q. Xin, and C. Li, Angew. Chem. Int. Ed., 41, 821 (2002) https://doi.org/10.1002/1521-3773(20020301)41:5<821::AID-ANIE821>3.0.CO;2-A
  20. C. E. Song, J. W. Yang, and H. J. Ha, Tetrahedron: Asymmetry, 8, 841 (1997) https://doi.org/10.1016/S0957-4166(97)00074-8
  21. C. Bolm and A. Gerlach, Eur. J. Org. Chem., 21 (1998)
  22. B. B. Lohray, E. Nandanan, and V. Bhushan, Tetrahedron Letters, 35, 6559 (1994) https://doi.org/10.1016/S0040-4039(00)78272-4
  23. C. E. Song, J. W. Yang, H. J. Ha, and S. G. Lee, Tetrahedron: Asymmetry, 7, 645 (1996) https://doi.org/10.1016/0957-4166(96)00054-7
  24. U. Kragl and T. Dwars, TRENDS in Biotechnology, 19, 442 (2001) https://doi.org/10.1016/S0167-7799(01)01766-8
  25. D. Brunel, N. Bellocq, P. Sutra, A. Cauvel, M. Lasperas, P. Moreau, F. D. Renzo, A. Galarneau, and F. Fajula, Coordination Chemistry Reviews, 178, 1085 (1998) https://doi.org/10.1016/S0010-8545(98)00121-0
  26. S. W. Kim, S. J. Bae, T. Hyeon, and B. M. Kim, Microporous and Mesoporous Materials, 44, 523 (2001) https://doi.org/10.1016/S1387-1811(01)00230-X
  27. A. Heckel and D. Seebach, Angew. Chem., Int. Ed. Engl., 39, 163 (2000) https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1<163::AID-ANIE163>3.0.CO;2-J
  28. M. J. Sabater, A. Corma, A. Domenech, V. Fornes, and H. Garcia, Chem. Commun., 1285 (1997)
  29. S. B. Ogunwumi and T. Bein, Chem. Commun., 901 (1997)
  30. C. Schuster and W. F. Holderich, Catal. Today, 60, 193 (2000) https://doi.org/10.1016/S0920-5861(00)00336-9
  31. L. Frunza, H. Kosslick, H. Landmesser, E. Hoft, and R. Fricke, J. Mol. Catal. A: Chemical, 123, 179 (1997) https://doi.org/10.1016/S1381-1169(97)00046-0
  32. P. Piaggio, P. Mcmorn, C. Langham, D. Bethell, P. C. Bulman-Page, F. E. Hancock, and G. J. Hutchings, New J. Chem., 1167(1998)
  33. H. H. Wagner, H. Hausmann, and W. F. Holderich, J. Catal., 203, 150 (2001) https://doi.org/10.1006/jcat.2001.3296
  34. S. Itsuno, M. Sakakura, and K. Ito, J. Org. Chem., 55, 6047 (1990) https://doi.org/10.1021/jo00311a024
  35. C. Franot, G. B. Stone, P. Engeli, C. Spondlin, and E. Waldvogel, Tetrahedron: Asymmetry, 6, 2755 (1995) https://doi.org/10.1016/0957-4166(95)00365-V
  36. S. Itsuno, Y. Sakurai, and K. Ito, POLYMER, 28, 1005 (1987) https://doi.org/10.1016/0032-3861(87)90177-7