A novel catalytic cycle for the synthesis of epoxides using sulfur ylides

Chemistry - A European Journal

Volumn 2, Issue 8, 1996, Pages 1024-1030

  Aggarwal, Varinder K ^a   Abdel Rahman, Hesham ^a   Fan, Li ^a   Jones, Ray V H ^b   Standen, Mike C H ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Catalysis; Diazo compounds; Epoxidations; Sulfur ylides; Synthetic methods

Indexed keywords

CATALYTIC QUANTITIES; DIAZO COMPOUNDS; ELEVATED TEMPERATURE; LOW CONCENTRATIONS; SULFIDE CONCENTRATION; SULFUR YLIDES; SYNTHETIC METHODS; TRANSITION METAL SALTS;

ALDEHYDES; CATALYSIS; EPOXIDATION; FUNCTIONAL GROUPS; KETONES; REACTION RATES; SULFUR; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

SULFUR COMPOUNDS;

EID: 0000554243     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020819     Document Type: Article

References (52)

1. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353.
2. B. M. Trost, L. S. Melvin, Sulfur Ylides, Academic Press, New York, 1975.
3. C. R. Johnson in Comprehensive Organic Chemistry (Eds.: D. H. R. Barton, W. D. Ollis), Pergamon Press, Oxford, 1979, Vol. 3, pp. 247.
4. A. C. Knipe in The Chemistry of the Sulphonium Group (Ed.: C. J. M. Stirling), Wiley, New York, 1981, pp. 313.
5. E. Block in The Chemistry of the Sulphonium Group (Ed., C. J. M. Sirling), Wiley, New York, 1981, pp. 673.
6. G. Robertson in Comprehensive Organic Synthesis (Eds.: B. M. Trost and I. Fleming), Pergamon Press, Oxford, 1991, Vol. 3, pp. 563.
7. Y. G. Gololobov, A. N. Nesmeyanov, V. P. Lysenko, I. E. Boldeskul, Tetrahedron 1987, 43, 2609.
8. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1962, 84, 867.
9. A. Padwa, S. F. Hornbuckle, Chem. Rev. 1991, 91, 263.
10. W. Ando, Acc. Chem. Res. 1977, 10, 179.
11. M. P. Doyle, Acc. Chem. Res. 1986, 19, 348.
12. M. P. Doyle, Chem. Rev. 1986, 86, 919.
13. G. Mass, Top. Stereochem. 1987, 137, 75.
14. J. Adams, D. M. Spero, Tetrahedron 1991, 47, 1765.
15. V. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, H. Y. Lee, B. D. Reid, J. Am. Chem. Soc. 1994, 116, 5973.
16. K. W. Ratts, A. N. Yao, J. Org. Chem. 1966, 31, 1689.
17. G. B. Payne, J. Org. Chem. 1968, 33, 3517.
18. A. W. Johnson, R. T. Amel, J. Org. Chem. 1969, 34, 1240.
19. K. O. Koua, M. E. Borredon, M. Delmas, A. Gaset, Synth. Commun. 1987, 17, 1593.
20. G. D. Buckley, L. H. Cross, N. H. Ray, J. Chem. Soc. 1950, 2714.
21. Y. V. Tomilov, V. A. Dokichev, U. M. Dzhemilev, O. M. Nefedov, Russ. Chem. Rev. 1993, 62, 799.
22. C. G. Overberger, J. P. Anselme, J. Org. Chem. 1963, 28, 592.
23. M. P. Doyle, J. H. Griffin, V. Bagheri, R. L. Dorow, Organometallics 1984, 3, 53.
24. B. K. R. Shankar, H. Shechter, Tetrahedron. Lett. 1982, 23, 2277.
25. M. J. Hatch, J. Org. Chem. 1969, 34, 2133.
26. G. R. Krow, Tetrahedron 1987, 43, 3.
27. M. P. Doyle, D. van Leusen, W. H. Tamblyn, Synthesis 1981, 1981, 787.
28. B. M. Trost, M. J. Bogdanowicz, J. Am. Chem. Soc. 1973, 95, 5298.
29. V. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, M. C. H. Standen, Tetrahedron. Lett. 1995, 36, 1731.
30. E. Borredon, M. Delmas, A. Gaset, Tetrahedron. Lett. 1982, 23, 5283.
31. M. E. Borredon, M. Delmas, A. Gaset, Tetrahedron 1987, 43, 3945.
32. M. P. Doyle, L. J. Westrum, W. N. E. Wolthuis, M. M. See, W. P. Boone, V. Bagheri, M. M. Pearson, J. Am. Chem. Soc. 1993, 115, 958.
33. A. Padwa, D. J. Austin, A. T. Price, M. A. Semones, M. P. Doyle, M. N. Protopopova, W. R. Winchester, A. Tran, J. Am. Chem. Soc. 1993, 115, 8669.
34. D. S. Brown, M. C. Elliott, C. J. Moody, T. J. Mowlem, J. P. Marino, A. Padwa, J. Org. Chem. 1994, 59, 2447.
35. A. Padwa, D. J. Austin, Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
36. M. P. Doyle, R. E. Austin, A. S. Bailey, M. P. Dwyer, A. B. Dyatkin, A. V. Kalinin, M. M. Y. Kwan, S. Liras, C. J. Oalmann, R. J. Pieters, M. N. Protopopova, C. E. Raab, G. H. P. Roos, Q. L. Zhou, S. F. Martin, J. Am. Chem. Soc. 1995, 117, 5763.
37. M. P. Doyle, Recl. Trav. Chim. Pays-Bas 1991, 110, 305.
38. R. G. Salomon, J. K. Kochi, J. Am. Chem. Soc. 1973, 95, 3300.
39. H. Nozaki, S. Moriuti, M. Yamabe, R. Noyori, Tetrahedron. Lett. 1966, 59.
40. There is only one example in the literature where the issue of trans:cis selectivity is addressed (A. W. Johnson, V. J. Hruby, J. L. Williams, J. Am. Chem. Soc. 1964, 86, 918). In this paper, high trans selectivity was obtained with diphenyl-sulfonium benzylide. It is therefore surprising that methylphenylsulfonium benzylide only gave a 77:23 ratio of trans:cis epoxides.
41. R. S. Drago, J. H. Long, R. Cosmano, Inorg. Chem. 1981, 20, 2920.
42. A. M. Dennis, R. A. Howard, D. Lacon, K. M. Kadish, J. L. Bear, J. Chem. Soc. Chem. Commun. 1982, 399.
43. S. A. Johnson, H. R. Hunt, H. M. Newmann, Inorg. Chem. 1963, 960.
44. G. H. P. Roos, M. A. McKervey, Synth. Comnun. 1992, 22, 1751.
45. W. C. Fernelius, B. E. Bryant, Inorg. Synth. 1957, 5, 105.
46. X. Creary, Org. Synth. 1985, 64, 207.
47. M. Imuta, H. Ziffer, J. Org. Chem. 1979, 44, 2505.
48. N. Furukawa, Y. Sugihara, H. Fujihara, J. Org. Chem. 1989, 54, 4222.
49. M. Shimagaki, Y. Matsuzaki, I. Hori, T. Nkata, T. Oishi, Tetrahedron. Lett. 1984, 4779.
50. V. R. Valent, J. L. Wolfhagen, J. Org. Chem. 1966, 31, 2509.
51. Y. Tumura, S. M. Bayomi, K. Sumoto, M. Ikeda, Synthesis 1977, 693.
52. T. Harada, E. Akiba, A. Oku, J. Am. Chem. Soc. 1983, 105, 2771.