Carbodiimide-Promoted Olefin Epoxidation with Aqueous Hydrogen Peroxide

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2564-2573

  Majetich, George ^a   Hicks, Rodgers ^a   Sun, Guang Ri ^a   McGill, Patrick ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001276944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972026n     Document Type: Article

References (55)

1. Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 357-436.
2. Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis Wiley-Interscience: New York, 1967; Vol. 1, p 135.
3. (a) Heaney, H. Aldrichimica Acta 1993, 26, 35.
4. (b) Heaney, H. Topics Current Chem. 1993, 164, 1.
5. (c) Cooper, M. S.; Heaney, H.; Newbold, A.; Sanderson, W. Synlett 1990, 533 and references therein.
6. (d) Muzart, J. Synthesis 1995, 1325.
7. (e) McKillop, A.; Sanderson, W. R. Tetrahedron 1995, 51, 6145.
8. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
9. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
10. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
11. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
12. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
13. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
14. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
15. For recent epoxidation procedures, see: (a) Murray, R.; Singh, M.; Williams, B.; Moncrieff, H. J. Org. Chem. 1996, 61, 1830. (b) Yang, D.; Yip, Y.; Tang, M.; Wong, M.; Zheng, J.; Cheung, K. J. Am. Chem. Soc. 1996, 118, 491. (c) Zhang, W.; Loebach, J.; Wilson, S.; Jacobsen, E. J. Am. Chem. Soc. 1990, 112, 2801. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063. (e) Zhang, W.; Jacobsen, E. J. Org. Chem. 1991, 56, 2296. (f) Sato, K.; Aoki, M.; Oagawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (g) Sharpless, K. B.; Rudollph, J.; Reddy, K. L.; Chiang, J. P. J. Am. Chem. Soc. 1997, 119, 6189. (h) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. Ibid. 1997, 119, 11224.
16. Strukul, G., Ed. Catalytic Oxidation with Hydrogen Peroxide as Oxidant; Kluwer: Dordrecht, Netherlands, 1992.
17. (a) Venturello, C.; Abneri, M.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
18. (b) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553.
19. Reynaud, J.; Battioni, P.; Bartoli, J.; Mansuy, D. J. Chem. Soc., Chem. Commun. 1985, 888.
20. Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42, 2034.
21. Heggs, R. P.; Ganem, B. J. Am. Chem. Soc. 1979, 101, 2484.
22. (a) Ho, T. L. Synth. Commun. 1979, 37.
23. (b) Rebek, J.; McCready, R. Tetrahedron Lett. 1979, 4337.
24. Martin, L. D.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 3511.
25. Chen, Y.; Reymond, J. Tetrahedron Lett. 1995, 36, 4015.
26. (a) Payne, G.; Deming, P.; Williams, P. J. Org. Chem. 1961, 26, 659.
27. (b) Payne, G. Tetrahedron 1962, 18, 763.
28. (a) Dulcere, J.-P.; Rodriguez, J. Tetrahedron Lett. 1982, 23, 1887.
29. (b) Rodriguez, J.; Dulcere, J.-P. J. Org. Chem. 1991, 56, 469.
30. (a) Rebek, J.; McCready, R.; Wolf, S.; Mossman, A. J. Org. Chem. 1979, 44, 1485.
31. (b) Rebek, J.; Wolf, S.; Mossman, A. J. Org. Chem. 1978, 43, 180.
32. R. McCready, Ph.D. Dissertation, University of Pittsburgh, 1980.
33. S. Wolf, Ph.D. Dissertation, University of California, Los Angeles, 1977.
34. Krishnan, S.; Kuhn, D.; Hamilton, G. Tetrahedron Lett. 1977, 1369.
35. Rebek, J.; Wolf, S.; Mossman, A. J. Chem. Soc., Chem. Commun. 1974, 711.
36. Rebek, J.; Wolf, S.; Mossman, A. Abstracts of the 172nd National Meeting of the American Chemical Society, ORGN 109, 1976.
37. Majetich, G.; Hicks, R. Synlett 1996, 649.
38. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society; Washington, DC, 1990; p 7. To prevent the accumulation of peroxides these solutions were prepared fresh for each use.
39. (a) Kingzett, C. J. Chem. Soc. 1880, 37, 792.
40. (b) Schimpf, H. A Manual of Volumetric Analysis, Wiley: New York, 1909, p 214.
41. Sodium percarbonate in acetic acid is not useful for epoxidations, see: Ohta, A.; Ohta, M. Synthesis 1985, 216.
42. Henbest, H.; Wilson, R. J. Chem. Soc. 1957, 1958.
43. (a) Itoh, T.; Jitsukawa, K.; Kaneda, K.; Teranishi, S. J. Am. Chem. Soc. 1979, 101, 159.
44. (b) Finn, M.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J., Ed.; Academic Press: New York, 1985, Vol. 5, pp 247-308.
45. Mitchell, P. Org. Prep. Proceed. Int. 1990, 22(4), 534.
46. Barrelle, M.; Apparu, M. Bull. Soc. Chim. Fr. 1972, 2016.
47. House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: Reading, MA, 1972 and references therein.
48. (a) Paquette, L.; Barrett, J. Org. Synth. 1969, 49, 62.
49. (b) Renolen, P.; Ugelstad, J. J. Chim. Phys. 1960, 57, 634.
50. (c) Curci, R.; DiPrete, R.; Edwards, J.; Modena, G. J. Org. Chem. 1970, 35, 740.
51. (d) Kavcic, R.; Plesnicar, B. J. Org. Chem. 1970, 35, 2033.
52. For the preparation of polymer-bound anhydrides, see: Scott, L.; Rebek, J.; Oysyanko, L.; Sims, C. J. Am. Chem. Soc. 1974, 96, 1606.
53. (a) Carlson, R.; Behn, N. J. Org. Chem. 1967, 32, 1363.
54. (b) Vedejs, E.; Dent, W.; Kendall, J.; Oliver, P. J. Am. Chem. Soc. 1996, 118, 3556.
55. Harrison, C.; Hodge, P. J. Chem. Soc., Perkin Trans. 1 1976, 605.