The synthesis of alkenes via epi-phosphonium species: 1. An anti-Wittig elimination

Tetrahedron

Volumn 54, Issue 50, 1998, Pages 15345-15360

  Lawrence, Nicholas J ^a   Muhammad, Faiz ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Alkenes; Elimination reactions; Phosphines; Wittig reaction

Indexed keywords

ALCOHOL; ALKENE; BORANE DERIVATIVE; CERIUM; LITHIUM; PHOSPHONIUM DERIVATIVE; PHOSPHORUS;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032506604     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00959-4     Document Type: Article

References (47)

1. 1 Buss, A. D.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1985, 2307; Buss, A. D.; Cruse, W. B.; Kennard, O.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1984, 243; Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem., 1997, 529, 29.
2. 1 Buss, A. D.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1985, 2307; Buss, A. D.; Cruse, W. B.; Kennard, O.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1984, 243; Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem., 1997, 529, 29.
3. 1 Buss, A. D.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1985, 2307; Buss, A. D.; Cruse, W. B.; Kennard, O.; Warren, S.; J. Chem. Soc., Perkin Trans. 1, 1984, 243; Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem., 1997, 529, 29.
4. 2 Pelter, A.; Buss, D.; Pitchford, A. Tetrahedron Lett., 1985, 26, 5093; Pelter, A.; Smith, K.; Elgendy, S. M. A. Tetrahedron, 1993, 49, 7119; Pelter, A.; Buss, D.; Colclough, E.; Singaram, B. Tetrahedron, 1993, 49, 7077; Pelter, A. Pure and Applied Chem., 1994, 66, 223.
5. 2 Pelter, A.; Buss, D.; Pitchford, A. Tetrahedron Lett., 1985, 26, 5093; Pelter, A.; Smith, K.; Elgendy, S. M. A. Tetrahedron, 1993, 49, 7119; Pelter, A.; Buss, D.; Colclough, E.; Singaram, B. Tetrahedron, 1993, 49, 7077; Pelter, A. Pure and Applied Chem., 1994, 66, 223.
6. 2 Pelter, A.; Buss, D.; Pitchford, A. Tetrahedron Lett., 1985, 26, 5093; Pelter, A.; Smith, K.; Elgendy, S. M. A. Tetrahedron, 1993, 49, 7119; Pelter, A.; Buss, D.; Colclough, E.; Singaram, B. Tetrahedron, 1993, 49, 7077; Pelter, A. Pure and Applied Chem., 1994, 66, 223.
7. 2 Pelter, A.; Buss, D.; Pitchford, A. Tetrahedron Lett., 1985, 26, 5093; Pelter, A.; Smith, K.; Elgendy, S. M. A. Tetrahedron, 1993, 49, 7119; Pelter, A.; Buss, D.; Colclough, E.; Singaram, B. Tetrahedron, 1993, 49, 7077; Pelter, A. Pure and Applied Chem., 1994, 66, 223.
8. 3 Peterson, D. J. J. Org. Chem., 1968, 33, 780; Ager, D. J. Org. React., 1990, 38, 1.
9. 3 Peterson, D. J. J. Org. Chem., 1968, 33, 780; Ager, D. J. Org. React., 1990, 38, 1.
10. 4 Rémion, J.; Krief, A. Tetrahedron Lett., 1976, 3743.
11. 5 Denis, J. N.; Dumont, W.; Krief, A. Tetrahedron Lett., 1979, 4111.
12. 6 Lawrence, N. J.; Muhammad, F. J. Chem. Soc., Chem. Commun., 1993, 1187.
13. 7 Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 241.
14. 8 Anti synthesis: Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1985, 2307; Buss, A. D.; Warren, S. Tetrahedron Lett., 1983, 24, 3931.
15. 8 Anti synthesis: Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1985, 2307; Buss, A. D.; Warren, S. Tetrahedron Lett., 1983, 24, 3931.
16. 9 Syn synthesis: Greeves, N.; Warren, S. Tetrahedron Lett., 1986, 27, 259; Elliott, J.; Hall, D.; Warren, S. Tetrahedron Lett., 1989, 30, 601; Buss, A. D.; Mason, R.; Warren, S. Tetrahedron Lett., 1983, 24, 5293.
17. 9 Syn synthesis: Greeves, N.; Warren, S. Tetrahedron Lett., 1986, 27, 259; Elliott, J.; Hall, D.; Warren, S. Tetrahedron Lett., 1989, 30, 601; Buss, A. D.; Mason, R.; Warren, S. Tetrahedron Lett., 1983, 24, 5293.
18. 9 Syn synthesis: Greeves, N.; Warren, S. Tetrahedron Lett., 1986, 27, 259; Elliott, J.; Hall, D.; Warren, S. Tetrahedron Lett., 1989, 30, 601; Buss, A. D.; Mason, R.; Warren, S. Tetrahedron Lett., 1983, 24, 5293.
19. 10 Horner, L.; Hoffmann, H.; Wippel, H. G. Chem. Ber., 1958, 91, 61.
20. 11 'The Wittig Method to Alkenes', Lawrence, N. J. in Alkene Synthesis (Practical approaches series in Chemistry), ed. Williams, J. M. J. Oxford University Press, Oxford, 1996, 19-58.
21. 12 Torr, R. S.; Warren, S. J. Chem. Soc. Pak., 1979, 1, 15.
22. 13 Imamoto, T.; Takeyama, T.; Kusumoto, T. Chem. Lett., 1985, 1491; Imamoto, T.; Sato, K.; Johnson, C. R. Tetrahedron Lett., 1985, 26, 783.
23. 13 Imamoto, T.; Takeyama, T.; Kusumoto, T. Chem. Lett., 1985, 1491; Imamoto, T.; Sato, K.; Johnson, C. R. Tetrahedron Lett., 1985, 26, 783.
24. 14 Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc., 1985, 107, 5301.
25. 15 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
26. 15 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
27. 15 Hockless, D. C. R.; Kang, Y. B.; McDonald, M. A.; Pabel, M.; Willis, A. C.; Wild, S. B. Organometallics, 1996, 15, 1301; Li, X.; Robinson, K. D.; Gaspar, P. P. J. Org. Chem., 1996, 61, 7702; Huy, N. H. T.; Mathey, F. Synlett, 1995, 353 and references therein.
28. 16 Hockless, D. C. R.; McDonald, M. A.; Pabel, M.; Wild, S. B. J. Chem. Soc., Chem. Commun., 1995, 257 and references therein.
29. 17 Boche, G.; Schneider, D. R. Tetrahedron Lett., 1976, 3657.
30. 18 Buss, A. D.; Warren, S.; Leake, J. S.; Whitham, G. J. Chem. Soc., Perkin Trans. 1, 1983, 2215.
31. 19 Brown, K. M.; Lawrence, N. J.; Liddle, J.; Muhammad, F.; Jackson, D. A. Tetrahedron Lett., 1994, 35, 6733.
32. 20 Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Biochemistry, 1989, 28, 6984.
33. 21 Pettit, G.R., Singh, S. B.; Hamel, E.; Lin, C. M.; Alberts, D. S.; Garcia-Kendall, D. Experientia, 1989, 45, 209.
34. 22 Dark, G. G.; Hill, S. A.; Prise, V. E.; Tozer, G. M.; Pettit, G. R.; Chaplin, D. J. Cancer Research, 1997, 57, 1829.
35. 23 Roberts, T. G.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1, 1985, 1953.
36. 50 of cell growth inhibition (L1210, murine leukaemia cells) for Z-15b is 7 nM whilst that of E-15b is 20 nM.
37. 25 Gourdel, Y.; Ghanimi, A.; Pellon, P.; Le Corre, M. Tetrahedron Lett., 1993, 34, 1011.
38. 26 Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc., 1990, 112, 5244.
39. 27 Pellon, P. Tetrahedron Lett., 1992, 33, 4451.
40. 28 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett., 1968, 2199.; N. T. Anh, Top. Curr. Chem., Springer-Verlag, Berlin Heidelberg, 1980, 88, 145.
41. 28 Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett., 1968, 2199.; N. T. Anh, Top. Curr. Chem., Springer-Verlag, Berlin Heidelberg, 1980, 88, 145.
42. 29 Grayson, J. I.; Norrish, H. K.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1976, 2556.
43. 30 Davidson, A. H.; Fleming, I.; Grayson, J. I.; Pearce, A.; Snowden, R. L.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1977, 550.
44. 31 Torr, R. S.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1983, 1173.
45. 32 Raunio, E. K.; Bonner, W. A. J. Org. Chem., 1966, 31, 396.
46. 33 Ishii, H.; Chen, I.-S.; Ishikawa, T. J. Chem. Soc., Perkin Trans. 1, 1987, 671.
47. 34 Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. J. Med. Chem., 1995, 38, 1666.