Polymeric catalysts for chemo- and enantioselective epoxidation of olefins: New crosslinked chiral transition metal complexing polymers

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 35, Issue 9, 1997, Pages 1809-1818

  De, Binod B ^a   Lohray, Braj B ^a   Sivaram, Swaminathan ^a   Dhal, Pradeep K ^a,b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b GENZYME CORPORATION   (United States)

Author keywords

Asymmetric synthesis; Chiral polymer; Polymer metal complex; Polymeric catalyst

Indexed keywords

CATALYSIS; CATALYSTS; COPOLYMERIZATION; CROSSLINKING; MANGANESE COMPOUNDS; MONOMERS; OLEFINS; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE EPOXIDATION; CHIRAL TRANSITION; ENANTIOSELECTIVE EPOXIDATION;

METALLORGANIC POLYMERS;

EID: 0031190853     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(19970715)35:9<1809::AID-POLA21>3.0.CO;2-8     Document Type: Article

References (51)

1. (a) P. K. Dhal, Ind. J. Technol., 31, 263 (1993);
2. (b) Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994).
3. (a) M. Zief and L. Crane, Eds., Chromatographic Chiral Separations, Dekker, New York, 1988;
4. (b) W. H. Pirkle and T. C. Pochapsky, Chem. Rev., 89, 347 (1989).
5. (a) M. Aglietto, E. Chiellini, S. D'Antone, G. Ruggeri, and R. Solaro, Pure Appl. Chem., 60, 415 (1988);
6. (b) G. Parrinello and J. K. Stille, J. Am. Chem. Soc., 109, 7122 (1987);
7. (c) S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Nakahama, and J. M. J. Fréchet, J. Org. Chem., 55, 304 (1990).
8. (a) H. Han and K. D. Janda, J. Am. Chem. Soc., 118, 7632 (1996);
9. (b) I. F. J. Vankelecom, D. Tas, R. F. Parton, V. V. de Vyver, and P. A. Jacobs, Angew. Chem. Int. Ed. Engl., 35, 1346 (1996).
10. (a) R. Sheldon, Chem. Ind., 212 (1990);
11. (b) V. Schurig and F. Betschinger, Chem. Rev., 92, 873 (1992);
12. (c) C. Blom, Angew. Chem. Int. Ed. Engl., 30, 403 (1991).
13. (a) Y. Naruta, F. Tani, N. Ishihara, and K. Maruyama, J. Am. Chem. Soc., 113, 6865 (1991);
14. (b) J. P. Collman, X. Zhang, V. J. Lee, E. S. Uffelman, and J. I. Braunman, Science, 261, 1404 (1993);
15. (c) K. Konishi, K.-I. Oda, K. Nishida, T. Aida, and S. Inoue, J. Am. Chem. Soc., 114, 1313 (1992).
16. (a) W. Zhang, J. L. Loebach, S. R. Wilson, and E. N. Jacobson, J. Am. Chem. Soc., 112, 2801 (1990);
17. (b) R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki, Tetrahedron Lett., 31, 7345 (1990);
18. (c) H. Sasaki, R. Irie, and T. Katsuki, Synlett, 300 (1993).
19. (a) E. N. Jacobson, in Catalytic Asymmetric Synthesis, I. Ojima, Ed., VCH; Weinheim, 1993, p. 159;
20. (b) R. Irie, N. Hosoya, and T. Katsuki, Synlett, 255 (1994).
21. (a) B. B. Lohray, A. Thomas, P. Chittari, J. Ahuja, and P. K. Dhal, Tetradedron Lett., 33, 5453 (1992);
22. (b) B. B. De, B. B. Lohray, and P. K. Dhal, Tetrahedron Lett., 34, 2371 (1993);
23. (c) B. B. De, B. B. Lohray, S. Sivaram, and P. K. Dhal, Macromolecules, 27, 1291 (1994).
24. B. B. De, B. B. Lohray, S. Sivaram, and P. K. Dhal, Tetrahedron Asymm., 6, 2105 (1995).
25. (a) F. R. Hartley, Supported Metal Catalysts, Reidel, Dordrecht, 1985;
26. (b) W. T. Ford, in Comprehensive Polymer Science, G. Allen, Ed., Pergamon, London, 1989, Vol. 6, p. 81;
27. (c) D. C. Sherrington, Pure Appl. Chem., 60, 401 (1988).
28. (a) J. M. J. Fréchet, Tetrahedron, 37, 663 (1981);
29. (b) P. Hodge, in Innovation and Perspectives in Solid Phase Synthesis, R. Epton, Eds., SPCC (UK) Ltd., Birmingham, 1990, p. 273.
30. (a) E. N. Jacobson, W. Zhang, and M. L. Guler, J. Am. Chem. Soc., 113, 6703 (1991);
31. (b) N. Hosoya, R. Irie, and T. Katsuki, SynLett, 261 (1993).
32. J. F. Larrow, E. N. Jacobson, Y. Gao, Y. Hong, X. Nie, and C. M. Zepp, J. Org. Chem., 59, 1939 (1994).
33. G. Wulff, Angew. Chem. Int. Edn. Engl., 34, 1812 (1995).
34. (a) E. J. Corey, R. Imwinkelried, S. Pikul, and Y. Xiang, J. Am. Chem. Soc., 111, 5493 (1989);
35. (b) K. Saigo, N. Kubota, S. Takebayashi, and M. Hasegawa, Bull. Chem. Soc. Jpn., 59, 931 (1986).
36. G. Wulff and A. Akelah, Makromol. Chem., 179, 2647 (1978).
37. A. Guyot, in Synthesis and Separation Using Functional Polymers, D. C. Sherrington, and P. Hodge, Eds., Wiley, New York, 1988, p. 1.
38. (a) P. K. Dhal and R. S. Khisti, Chem. Mater., 5, 1618 (1993);
39. (b) P. K. Dhal and F. H. Arnold, Macromolecules, 25, 7051 (1992).
40. K. Srinivasan, P. Michaud, and J. K. Kochi, J. Am. Chem. Soc., 108, 2309 (1986).
41. C. Bowers and P. K. Dutta, J. Catal., 122, 271 (1990).
42. (a) G. Wulff and J. Vietmeier, Makromol. Chem., 190, 1727 (1989);
43. (b) S. E. Byström, A. Boerje, and B. Akermark, J. Am. Chem. Soc., 115, 2081 (1993).
44. (a) R. Irie, K. Noda, N. Matsumoto, and T. Katsuki, Tetrahedron Asymm., 2, 481 (1991);
45. (b) K. Konishi, K.-I. Oda, K. Nishida, T. Aida, and S. Inoue, J. Am. Chem. Soc., 115, 2081 (1993).
46. J. P. Collman, V. J. Lee, C. J. Kellen-Yuen, X. Zhang, J. A. Ibers, and J. I. Brauman, J. Am. Chem. Soc., 117, 692 (1995).
47. (a) Z. Li, K. R. Conser, and E. N. Jacobson, J. Am. Chem. Soc., 115, 5326 (1993);
48. (b) K. Ito and T. Katsuki, Synlett, 638 (1993);
49. (c) T. Fukuda and T. Katsuki, Synlett, 825 (1995);
50. (d) Y. Yamashita and T. Katsuki, Synlett, 829 (1995).
51. A. I. Vogel, Textbook of Practical Organic Chemistry, 3rd ed., Longman, London, 1973, p. 541.