Polymer-supported salen complexes for heterogeneous asymmetric synthesis: stability and selectivity

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 37, Issue 21, 1999, Pages 3888-3898

  Angelino, Mark D ^a   Laibinis, Paul E ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; CATALYSTS; CHROMIUM; COMPLEXATION; DECOMPOSITION; DEGRADATION; ETHERS; MANGANESE; METALS; OLEFINS; OXIDATION; SYNTHESIS (CHEMICAL);

ASSYMETRIC SYNTHESIS; EPOXIDATION; HETEROGENEOUS CATALYSIS; POLYMER METAL COMPLEXES; POLYMER SUPPORTED SALEN COMPLEXES; SALEN LIGAND;

POLYMERS;

EID: 0033225020     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(19991101)37:21<3888::AID-POLA2>3.0.CO;2-B     Document Type: Article

References (62)

1. Bolm, G.; Gerlach, A. Eur J Org Chem 1998, 1, 21.
2. Blaser, H. Tetrahedron 1991, 2, 843.
3. Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Chapter 4, p 159.
4. Nugent, W.; Rajanbabu, T.; Burk, M. Science 1993, 259, 479.
5. Stinson, S. C. Chem Eng News 1993, 71, 38.
6. Penzien, K.; Schmidt, G. Angew Chem 1969, 81, 628.
7. Lahav, M.; Laub, F.; Gati, E.; Leiserowitz, L.; Ludmer, Z. J Am Chem Soc 1976, 98, 1620.
8. Toda, F. Topics in Current Chemistry 1988 149 211.
9. Stewart, T.; Lipkin, D. J Am Chem Soc 1939, 61, 3297.
10. Bartok, M.; Wittman, G.; Bartok, G.; Gondos, G. J Organometal Chem 1990, 384, 385.
11. Ogunwumi, S. B.; Bein, T. Chem Commun 1997, 9, 901.
12. Vankelecom, I. F. J.; Tas, D.; Parton, R. F.; Van de Vyver, V.; Jacobs, P. A. Angew Chem Int Ed Engl 1996, 35, 1346.
13. Minutolo, F.; Fini, D.; Pétri, A.; Salvador!, P. Tetrahedron Asymmetry 1996, 7, 2293.
14. Lohray, B. B.; Thomas, A.; Chittari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett 1992, 33, 5453.
15. De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Tetrahedron Asymmetry 1995, 6, 2105.
16. Zhang, W.; Jacobsen, E. N. J Org Chem 1991, 56, 2296.
17. Wei, Z.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J Am Chem Soc 1990, 112, 2801.
18. Larrow, J. F.; Jacobsen, E. N. J Org Chem 1994,59, 1939.
19. Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311.
20. Irie, R.; Noda, K; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett 1990, 31, 7345.
21. Chang, S.; Lee, N. H.; Jacobsen, E. N. J Org Chem 1993, 58, 6939.
22. Lee, N. H.; Jacobsen, E. N. Tetrahedron Lett 1991, 32, 6533.
23. Sheldon, R.; Kochi, J. In Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
24. O'Connor, K. J.; Wey, S. J.; Burrows, C. J. Tetrahedron Lett 1992, 33, 1001.
25. Kureshy, R.; Khan, N.; Abdi, S.; Bhatt, A. J Mol Catal A Chem 1996, 110, 33.
26. Li, Z.; Conser, K. R.; Jacobsen, E. N. J Am Chem Soc 1993, 115, 5326.
27. Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 7, 469.
28. Fukuda, T.; Katsuki, T. Synlett 1995, 8, 825.
29. Kaufman, M.; Grieco, P.; Bougie, D. J Am Chem Soc 1993, 115, 11648.
30. Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J Am Chem Soc 1996, 118, 7420.
31. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Guler, M. L.; Ishida, T.; Jacobsen, E. N. J Am Chem Soc 1998, 120, 948.
32. Jacobsen, E. N.; Zhang, W.; Guler, M. L. J Am Chem Soc 1991, 113, 6703.
33. Karjalainen, J.; Hormi, O.; Sherrington, D. Tetrahedron Asymmetry 1998, 9, 2019.
34. Karjalainen, J.; Hormi, O.; Sherrington, D. Tetrahedron Asymmetry 1998, 9, 1563.
35. Pini, D.; Petri, A.; Salvadori, P. Tetrahedron Asymmetry 1993, 4, 2351.
36. Kirn, B.; Sharpless, K. Tetrahedron Lett 1990, 31, 3003.
37. Song, C.; Yang, J.; Ha, H.; Lee, S. Tetrahedron Asymmetry 1996, 7, 645.
38. Han, H.; Janda, K. D. J Am Chem Soc 1996, 118, 7632.
39. Collman, J. P.; Lee, V. J.; Kellenyuen, C. J.; Zhang, X. M.; Ibers, J. A.; Braumna, J. I. J Am Chem Soc 1995, 117, 692.
40. Razenberg, J. A. S. J.; Nolte, R. J. M.; Drenth, W. Tetrahedron Lett 1984, 25, 789.
41. Zhao, S. H.; Ortiz, P. R.; Keys, B. A.; Davenport, K. G. Tetrahedron Lett 1996, 37, 2725.
42. Hughes, D. L.; Smith, G. B.; Liu, J.; Dezeny, G. C.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J Org Chem 1997, 62, 2222.
43. De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. J Polym Sci Part A Polym Chem 1997, 35, 1809.
44. Minutolo, F.; Fini, D.; Salvador!, P. Tetrahedron Lett 1996, 37, 3375.
45. Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 31, 7581.
46. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827.
47. Brandes, B. D.; Jacobsen, E. N. J Org Chem 1994, 59, 4378.
48. Chang, S. In Highly Enantioselective Catalytic Routes to Trans Epoxides by Manganese Complexes; Harvard University: Cambridge, 1996; p 190.
49. Kureshy, R. L; Khan, N. H.; Abdi, S. H. R.; lyer, P. J React Funct Polym 1997, 34, 153.
50. De, B. B.; Lohray, B. B.; Sivaram, S.; Dhal, P. K. Macromolecules 1994, 27, 1291.
51. We also examined the stability of the ethereal tether to the reaction conditions using benzyl phenyl ether as a homogeneous model compound for the heterogeneous link. We exposed a solution of this compound to NaOCl under the conditions for the heterogeneous reactions and characterized aliquots of the solution by gas chromatography to quantify the loss of this compound against an internal standard (chlorobenzene). We consistently observed degradation of the ether and formation of benzaldehyde, indicating the ability of this linkage to fragment under the reaction conditions.
52. Alternate chemistries of attachment were evaluated to provide a covalent link between the salen complex and the polymer that would be able to withstand the oxidative conditions for epoxidation. We examined the suitability of using sulfide and sulfone links for the ligand using model compounds. Under the epoxidation conditions, the sulfide link cleaved readily while the sulfone link did not fracture through 24 h of exposure to the epoxi.dation conditions. As our evidence noted fracture of the salen ligand under the epoxidation conditions, we did not further investigate the use of this link in a heterdgenized catalyst. These studies are described in: Angelino, M. D., Ph.D. Thesis, MIT, 1999.
53. Fraile, J. M.; Garcia, J. L; Massam, J.; Mayoral, J. A. J Mol Catal A Chem 1998, 136, 47.
54. Senanayake, C. H.; Smith, G. B.; Ryan, K. M.; Fredenburgh, L. E.; Liu, J.; Roberts, F. E.; Hughes, D. L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett 1996, 37, 3271.
55. The use of donor ligands for the heterogeneous complex was also attempted without enhancement of recyclability.
56. We examined the heterogeneous catalyst (2) using m-CPBA with 4-methylmorpholine-7V-oxide (NMO). The latter compound forms a salt with the oxidant and prevents the competing reaction between the oxidant and olefin to produce a racemic product. We observed that the heterogeneous catalyst using m-CPBA/NMO as oxidant also exhibited decreased activity and enantioselectivity upon recycle.
57. Martinez, L. E.; Leighton, J. L.; Garsten, D. H.; Jacobsen, E. N. J Am Chem Soc 1995, 117, 5897.
58. Tsai, C. C.; Follis, K E.; Sabo, A.; Beck, T. W.; Grant, R. F.; Bischofberger, N.; Benveniste, R. E.; Black, R. Science 1995, 270, 1197.
59. Wang, Z. M.; Zhang, X. L.; Sharpless, K. B. Tetrahedron Lett 1993, 34, 2267.
60. Galsbol, F.; Steenbol, P.; Sorenson, B. S. Acta Chem Scand 1972, 26, 3605.
61. Tu, Y.; Wang, Z. X.; Shi, Y. J Am Chem Soc 1996, 118, 9806.
62. Ayres, J. T.; Mann, C. K Polymer Letters 1965,3, 505.