Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 9. New reagents for amination of the ethylenic linkage

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 9, 1978, Pages 1090-1100

  Barton, Derek H R ^a   Britten Kelly, Michael R ^a   Ferreira, Daneel ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049109263     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19780001090     Document Type: Article

References (44)

1. N. Schonberger and G. Kresze, Annalen, 1975, 1725.
2. K. B. Sharpless and T. Hori, J. Org. Chem., 1976, 41, 176.
3. K. B. Sharpless, T. Hori, L. K. Truesdale, and C. O. Dietrich, J. Amer. Chem. Soc, 1976, 98, 269.
4. K. B. Sharpless and S. P. Singer, J. Org. Chem., 1976, 41, 2504.
5. K. B. Sharpless, A. O. Chong, and K. Oshima, J. Org. Chem., 1976, 41, 177.
6. E. S. Levchenko and L. V. Seleznenko, J. Org. Chem. (U.S.S.R.), 1970, 6, 486.
7. Y. Ueno, S. Takemura, Y. Ando, and H. Zerauchi, Chem. and Pharm. Bull. (Japan), 1967, 15, 1193.
8. G. L. Closs and S. J. Brois, J. Amer. Chem. Soc, 1960, 82, 6068.
9. R. Pummerer, Ber., 1909, 42, 2282; 1910, 43, 1401.
10. W. E. Parhan and R. Koncos, J. Amer. Chem. Soc, 1961, 83, 4034.
11. W. E. Parhan, L. Christensen, S. H. Groen, and R. M. Dob- son, J. Org. Chem., 1964, 29, 2211.
12. D. H. R. Barton and R. C. Cookson, Quart. Rev., 1956,10, 44.
13. A. Hassner and C. C. Heathcock, Tetrahedron Letters, 1964, 1125
14. J. Org. Chem., 1964, 29, 1350.
15. A. Hassner and C. C. Heathcock, J. Org. Chem., 1965, 30, 1748.
16. H. G. Kuivila, L. W. Menapace, and C. R. Warne, J. Amer. Chem. Soc, 1962, 84, 3854.
17. H. G. Kuivila and L. W. Menapace, J. Org. Chem., 1963, 28, 2165.
18. C. W. Shoppee, J. G. Feher, R. M. Hall, R. E. Lack, and L. Tarasoff, J. Chem. Soc (C), 1968,17, 2211.
19. G. M. Badger, H. J. Rodda, and W. H. F. Sasse, J. Chem. Soc, 1954, 4162.
20. H. G. Kuivilla, J. Org. Chem., 1961, 25, 284.
21. K. Murato, T. Shiori, and S. I. Yamada, Chem. and Pharm. Bull. (Japan), 1977, 25, 1559.
22. S. Takemura, K. Otsuki, K. Okamoto, and Y. Ueno, Chem. and Pharm. Bull. (Japan), 1968, 16, 1881, 1885.
23. A. J. Speziale, K. W. Ratts, and G. J. Maxo, J. Org. Chem., 1961, 26, 4311.
24. I. R. Alexander and H. McCombie, J. Chem. Soc, 1932, 2087.
25. G. Bullmer and F. G. Mann, J. Chem. Soc, 1945, 666.
26. For a review, see D. S. Klayman, ' Organic Selenium Compounds: their Chemistry and Biology,' eds. D. S. Klayman and W. H. H. Giinther, Wiley-Interscience, New York, 1974, p. 97.
27. W. H. Mueller and P. E. Butler, J. Amer. Chem. Soc, 1968, 90, 2075.
28. G. H. Schmid and D. G. Garratt,' Double Bonded Functional Groups,' Supplement A, ed. S. Patai, Wiley, New York, 1976, p. 1725.
29. D. G. Garratt and G. H. Schmid, J. Org. Chem., 1977, 42, 1776.
30. D. T. McAllan, T. V. Cullum, R. A. Dean, and F. A. Filder, J. Amer. Chem. Soc, 1951, 73, 3627.
31. A. Schonberg, E. Singer, E. Frese, and K. Praefcke, Chem. Ber., 1965, 98, 3311.
32. D. L. Klayman and T. S. Griffin, J. Amer. Chem. Soc, 1973, 95, 197.
33. L. Colichman and D. L. Dove, J. Amer. Chem. Soc, 1953, 75, 5736.
34. E. Vinkler and F. Klivenyi, Acta Chim. Acad. Sci. Hung., 1954, 5, 159.
35. S. G. Clarke, J. Kenyon, and H. Phillips, J. Chem. Soc, 1930, 1225.
36. G. Denzer, P. Allen, P. Conway, and J. M. van der Veen, J. Org. Chem., 1966, 31, 3418.
37. D. M. Hall and E. E. Turner, J. Chem. Soc, 1945, 694.
38. Y. Okamoto, K. L. Chellappa, and R. M. Homsany, J. Org. Chem., 1973, 38, 3172.
39. A. E. Kretov, E. A. Abrazhanova, S.I. Zlotchenko, and V. P. Kukchar, Zhur. obshchei Khim., 1963, 33, 2355.
40. R. B. Boar, D. W. Hawkins, J. F. McGhie, and D. H. R. Barton, J.C.S. Perkin I, 1973, 654.
41. R. Sasin, F. R. Longo, F. A. Carey, C. M. Paulson, and G. S. Sasin, J. Amer. Oil Chemists' Soc, 1960, 37, 152.
42. K. B. Sharpless and R. F. Lauer, J. Amer. Chem. Soc, 1973, 95, 2697.
43. P. A. Briscoe, F. Challenger, and P. S. Duckworth, J. Chem. Soc, 1965, 1755.
44. W. Klotzer, Monatsh., 1970, 101. 1841.