Selective Epoxidation of Olefins by Perfluoro-cis-2,3-dialkyloxaziridines 1

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8805-8810

  Arnone, Alberto ^a   Desmarteau, Darryl D ^b   Novo, Barbara ^c   Petrov, Viacheslav A ^d   Pregnolato, Massimo ^a   Resnati, Giuseppe ^b  

^a CLEMSON UNIVERSITY   (United States)

^b CNR   (Italy)

^c UNIVERSITY OF PAVIA   (Italy)

^d DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001260730     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961196h     Document Type: Article

References (75)

1. Presented in part at the 13th International Symposium on Fluorine Chemistry; Bochum, Germany, Sept 1-6, 1991; Book of Abstracts, p 149.
2. Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 357.
3. Sharpless, K. B.; Finn, M. G. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 8.
4. Zeller, K.-P. In Houben-Weyl Methoden der Organischen Chemie; Kröpf, H., Ed.; Thieme Verlag: Stuttgart, 1988; E 13.
5. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
6. (a) The Chemistry of Peroxides; Patai, S., Ed.; Wiley: New York, 1983.
7. (b) Organoperoxo Compounds. Houben-Weyl Methoden der Organischen Chemie; Kröpf, H., Ed.; Thieme Verlag: Stuttgart, 1988; E 13, Parts l and 2.
8. Bruice, T. C. Aldrichimica Acta 1988, 21, 87.
9. Hean'ey, H. Aldrichimica Acta 1993, 26, 35.
10. Rebek, J., Jr. Heterocydes 1981,15, 517.
11. Butler, A.; Clague, M. J.; Meister, G. E. Chem. Rev. 1994, 94, 625.
12. Conte, V.; Di Furia, F.; Modena, G. In The Chemistry of Functional Group, Organic Peroxides; Ando, W., Ed.; John Wiley & Sons: Chichester, 1992; p 559.
13. Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 389.
14. Mimoun, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 734.
15. Pfenninger, A. Synthesis 1986, 89.
16. Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391.
17. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989,22, 205.
18. Murray, R. W. Chem. Rev. 1989,89, 1187.
19. Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, Chapter 1.
20. Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
21. Schmilz, E. In Comprehensive Heterocyclic Chemistry; Lwowski, W. Ed.; Pergamon Press: Oxford, 1984; Vol. 7, part 5, p 195.
22. Davis, F. A.; Thimma Reddy, R.; Han, W.; Reddy, R. Pure Appl. Chem. 1993, 65, 633.
23. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919.
24. Petrov, V. A.; Resnati, G. Chem. Rev. 1996, 96, 1809.
25. (a) DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1994, 59, 2762.
26. (b) Terreni, M.; Pregnolato, M.; Resnati, G.; Benfenati, E. Tetrahedron 1995,57, 7981.
27. Bègue, J.-P.; M'Bida, A.; Bonnet-Delpon, D.; Novo, B.; Resnati, G. Synthesis 1996, 399.
28. (a) Balsarini, C.; Novo, B.; Resnati, G. J. Fluorine Chem. 1996, 80, 47.
29. (b) Bernardi, R.; Novo, B.; Resnati, G. J. Chem. Soc., Perkin Trans, l 1996, 2517.
30. Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329.
31. DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. Tetrahedron Lett. 1992, 33, 7245.
32. Arnone, A.; Bernardi, R.; Cavicchioli, M.; Resnati, G. J. Org. Chem. 1995, 60, 2314.
33. (a) DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 775, 4897.
34. (b) Arnone, A.; Cavicchioli, M.; Montanari, V.; Resnati, G. J. Org. Chem. 1994, 59, 5511.
35. Cavicchioli, M.; Mêle, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901.
36. 13C satellite peaks. The value of the 4.2 Hz proves a cis configuration. By using the same methodology, the oxirane protons H-ll and H-12 of compound 3h showed a coupling constant of 2.3 Hz, which indicates a trans relationship.
37. Weinkam, R. J. J. Am. Chem. Soc. 1974, 1032.
38. Mori, K.; Suguro, T.; Uehida, M. Tetrahedron 1978, 34, 3119.
39. Fraile, J. M.; Garcia, J. L; Mayoral, J. A.; de Mènorval, L. C.; Rachdi, F. J. Chem. Soc., Chem. Commun. 1995, 539.
40. Prandi, J.; Kagan, H. B.; Mimoun, H. Tetrahedron Lett. 1986, 27, 2617.
41. Miyashita, M.; Suzuki, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1989, 111, 3278.
42. 3-14.
43. Shoppee, C. W.; Summers, G. H. R. J. Chem. Soc. 1952, 1790.
44. 3-19 enhanced both the epoxide proton, H-2 (1.5) and H-3 (2) for 31 and H-ll (4) and H-12 (3) for 3t, respectively.
45. Burnett, R. D.; Kirk, D. N. J. Chem. Soc., Ferkln Trans, l 1973, 1830.
46. Henbest, H. B.; Jackson, W. R. J. Chem. Soc. C 1967, 2459.
47. Jankowski, K; Daigle, J.-Y. Synthesis 1971, 32.
48. The stereochemistry of 5,6-epoxy steroids 3n-s was established from the behavior of the H-6 resonance, which is known to appear as a doublet at 2.9 ppm ca. (J ≃ 4 Hz) in the a isomer and as a doublet at 3.1 ppm ca. (J ≃ 2 Hz) in the β isomer (refs 28, 29).
49. Galagovsky, L. R.; Gros, E. G. J. Chem. Res., Synop. 1990, 366.
50. Yamada, T.; Imagawa, K.; Mukaiyama, T. Chem. Lett. 1992, 2109.
51. Linskeseder, M.; Zbiral, E. Liebigs Ann. Chem. 1978, 1076.
52. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mineione, E. Tetrahedron Lett. 1994, 35, 935.
53. Lluch, A.-M.; Sânchez-Baeza, F.; Messeguer, A. Tetrahedron 1993, 49, 6299.
54. Jones, C. W.; Sankey, J. P.; Sanderson, W. R.; Rocca, M. C.; Wilson, S. L. J. Chem. Res., Synop. 1994,3,114.
55. Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758.
56. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
57. Davis, F. A.; Abdul-Malik, N. F.; Awad, S. B.; Karakal, M. E. Tetrahedron Lett. 1981, 917.
58. Seiter, G. A.; McMichael, K. D. J. Org. Chem. 1967,32, 2546.
59. Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett. 1990, 533.
60. Astudillo, L.; Galindo, A.; Gonzalez, A. G.; Mansilla, H. Heterocydes 1993, 36, 1075.
61. Ramasseul, R.; Tavarès, M.; Marchon, J.-C. J. Chem. Res., Synop. 1992, 104.
62. Marchon, J.-C.; Raraasseul, R. Synthesis 1989, 389.
63. Tavarès, M.; Ramasseul, R.; Marchon, J.-C.; Bachet, B.; Brassy, C.; Mornon, J.-P. J. Chem. Soc., Perkin Trans. 2 1992, 1321.
64. Marples, B. A.; Muxworthy, J. P.; Baggaley, K. H. Tetrahedron Lett. 1991, 32, 533.
65. Kimura, M.; Muto, T. Chem. Pharm. Bull. 1980, 28, 1836.
66. Mastrorilli, P.; Nobile, C. F.; Suranna, G. P.; Lopez, L. Tetrahedron, 1995, 51, 7943.
67. Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830.
68. Petrov, V. A.; DesMarteau, D. D. J. Org. Chem. 1993,58,4154.
69. Petrov, V. A.; DesMarteau, D. D. J. Chem. Soc., Perkin Trans, l 1993, 505.
70. Claus, P. K.; Vierhapper, F. W. J. Org. Chem. 1977, 42, 4016.
71. Johnson, C. R.; Rogers, P. E. J. Org. Chem. 1973, 38, 1793.
72. Deyrup, J. A.; Moyer, U. V. J. Org. Chem. 1969, 34, 1835.
73. Tori, K.; Komeno, T.; Nakagawa, T. J. Org. Chem. 1964, 29, 1136.
74. Jankowski, K.; Harvey, R. Synthesis 1972, 627.
75. Haire, M. J.; Boswell, G. A., Jr. J. Org. Chem. 1977, 42, 4251.