Soluble polymer-bound ligand-accelerated catalysis: Asymmetric dihydroxylation

Journal of the American Chemical Society

Volumn 118, Issue 32, 1996, Pages 7632-7633

  Han, Hyunsoo ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; CATALYSIS; HYDROXYLATION; REACTION ANALYSIS;

EID: 0029784123     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9608095     Document Type: Article

References (46)

1. (a) Pittman, C. U. Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982.
2. (b) Mathur, N. C.; Narang, C. K. Williams, R. E. Polymers as Aids in Organic Chemistry; Academic Press: New York, 1980.
3. (c) Frechet, J. M. J. Tetrahedron 1981, 37, 663.
4. (d) Syntheses and Separations Using Functionalized Poloymers; Sherrington, D. C., Hodge, P., Eds.; Wiley: New York, 1988.
5. (e) Bergbreiter, D. E.; Blanton, J. R.; Chandran, R.; Hein, M. D.; Huang, K.-J.; Treadwell, D. R.; Walker, S. A. J. Polym. Sci., Polym. Chem. Ed. 1989, 27, 4205.
6. Barany, G.; Merrifield, R. B. In The Peptides, Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, p 1.
7. (a) Bayer, E.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1975, 14, 493.
8. (b) Bayer, E.; Schurig, V. CHEMTECH 1976, 6, 212.
9. (c) Bergbreiter, D. E. ACS Symposium Series 1986, 308, 17.
10. (d) Bergbreiter, D. E.; Chandran, R. J. Am. Chem. Soc. 1987, 109, 174.
11. (e) Bergbreiter, D. E. CHEMTECH 1987, 17, 686.
12. (f) Phelps, J. C.; Bergbreiter, D. E. Tetrahedron Lett. 1989, 30, 3915.
13. (g) Bergbreiter, D. E.; Walker, S. A. J. Org. Chem. 1989, 54, 2726.
14. (i) Bergbreiter, D. E.; Morvant, M.; Chen, B. Tetrahedron Lett. 1991, 32, 2731.
15. (j) Doyle, M. P.; Eismont, M. Y.; Bergbreiter, D. E.; Gray, H. N. J. Org. Chem. 1992, 57, 6103.
16. (k) Bergbreiter, D. E.; Zhang, L.; Mariagnanam, V. M. J. Am. Chem. Soc. 1993, 115, 9295.
17. Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419.
18. Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539.
19. Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
20. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 116, 2483.
21. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 3003.
22. (b) Pini, D.; Petri, A.; Nardi, A.; Rosini, C.; Salvadori, P. Tetrahedron Lett. 1991, 32, 5175.
23. (c) Lohray, B. B.; Thomas, A.; Chihari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett. 1992, 33, 5453.
24. (d) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron: Asymmetry 1993, 4, 2351.
25. (e) Lohray, B. B.; Nandanan, E.; Bhushan, V. Tetrahedron Lett. 1994, 35, 6559.
26. (f) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron 1994, 50, 11321.
27. (g) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron Lett. 1995, 36, 1549.
28. (h) Sung, E. C.; Roh, E. J.; Lee, S.-G.; Kim, I. O. Tetrahedron: Asymmetry 1995, 6, 2687.
29. A recent report by Salvadori and co-workers describes an insoluble support that provides improved enantioselectivity. However, their system still required long reaction times (24 h) and excess of polymeric ligand. Furthermore, reaction yields were lower than observed under homogeneous reaction conditions. Petri, A.; Pini, D.; Rapaccini, S.; Salvadori, P. Chirality 1995, 7, 580.
30. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
31. 2-PHAL ligand has been appended to MeO-PEG; this new liquid phase ligand provides significantly greater enantioselectivity (Han, H.; Janda, K. D. Unpublished results).
32. (a) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Nayori, R. J. Am. Chem. Soc. 1987, 109, 1596.
33. (b) Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.
34. (c) Lowenthal, R. E.; Masasmune, S. Tetrahedron Lett. 1991, 32, 7373.
35. (d) Li, Z.; Cosner, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
36. (e) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D.M. J. Am. Chem. Soc. 1993, 115, 5328.
37. (f) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; pp 103-158.
38. (g) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993; pp 159-202.
39. (h) Li, G; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
40. (a) Steckhan, E.; Herrmann, S.; Ruppert, R.; Thommes, J.; Wandrey, C. Angew. Chem., Int. Ed. Engl. 1990, 29, 388.
41. (b) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
42. (c) Bergbreiter, D. E.; Zhang, L.; Mariagnanam, V. M. J. Am. Chem. Soc. 1993, 115, 9295.
43. (d) Horvath, I. T.; Rabai, J. Science 1994, 266, 72.
44. (a) Frisbee, A. R.; Nantz, M. H.; Kramer, G. W.; Fuchs, P. L. J. Am. Chem. Soc. 1984, 106, 7143.
45. (b) Sabadosa, G. J.; Fuchs, P. L.; Kramer, G. W. Lab. Rob. Automation 1989, 1, 265.
46. (c) Dewitt, S. H.; Czarnik, A. W. Current Opin. Biotech. 1995, 6, 640.