The stereochemistry of the vinylogous Peterson elimination

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 17, 1998, Pages 2749-2763

  Fleming, Ian ^a   Morgan, Ian T ^a   Sarkar, Achintya K ^a  

^a Department of Chemistry ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748655695     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804090g     Document Type: Article

References (64)

1. D. J. Ager, Org. React. (NY), 1990, 38, 1.
2. P. F. Hudrlik and D. Peterson, J. Am. Chem. Soc., 1975, 97, 1464.
3. A. G. Angoh and D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1984, 534.
4. I. Fleming, I. T. Morgan and A. K. Sarkar, J. Chem. Soc., Chem. Commun., 1990, 1575.
5. S. Rajagopalan and G. Zweifel, Synthesis, 1984, 111.
6. J. Meijer and P. Vermeer, Recl. Trav. Chim. Pays-Bas, 1974, 93, 183.
7. J. Ukai, Y. Ikeda, N. Ikeda and H. Yamamoto, Tetrahedron Lett., 1984, 25, 5173.
8. P. E. Sonnet and R. R. Heath, J. Chem. Ecol., 1980, 6, 221.
9. A. Suzuki, N. Miyaura, S. Abiko, M. Itoh, M. M. Midland, J. A. Sinclair and H. C. Brown, J. Org. Chem., 1986, 51, 4507.
10. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut and P. E. J. Sanderson, J. Chem. Soc., Perkin Trans 1, 1995, 317.
11. M. L. Mihailovic, R. Markovic and A. Milovanovic, Rad Jugosl. Akad. Znan. Umjet., Kem., 1986, 425, 53
12. (Chem. Abstr., 1988, 108, 94 312b).
13. S. Srivastava, J. Minore, C. K. Cheung and W. J. le Noble, J. Org. Chem., 1985, 50, 394.
14. S. T. Akhmedov, N. S. Sadykhov, R. S. Akhmedova and N. S. Zefirov, Khim. Ceterotsikl. Soedin., 1981, 1593;
15. Chem. Heterocycl. Compd. (Engl. Trans.), 1081, 17, 1158.
16. D. Gagnaire and P. Monzeglio, Bull. Soc. Chim. Fr., 1965, 474;
17. M. L. Mihailovic, R. I. Mamuzic, L. Zigic-Mamuzic, J. Bosnjak and Z. Cekovic, Tetrahedron, 1967, 23, 215.
18. C. Trindle, J.-T. Hwang and F. A. Carey, J. Org. Chem., 1973, 38, 2664;
19. M. Larchevêque and A. Debal, J. Chem. Soc., Chem. Commun., 1981, 877;
20. P. F. Hudrlik, A. M Hudrlik and A. K. Kulkarni, J. Am. Chem. Soc., 1982, 104, 6809.
21. M. Schlosser, O. Desponds, R. Lehmann, E. Moret and G. Rauchschwalbe, Tetrahedron, 1993, 49, 10 175;
22. A. Shibayama, T. Nakamura, T. Asada, T. Shintani, Y. Ukaji, H. Kinoshita and K. Inomata, Bull. Chem. Soc. Jpn., 1997, 70, 381.
23. I. Fleming, G. R. Jones, N. D. Kindon, Y. Landais, C. P. Leslie, I. T. Morgan, S. Peukert and A. K. Sarkar, J. Chem. Soc., Perkin Trans. 1, 1996, 1171.
24. F. Sato, Y. Suzuki and M. Sato, Tetrahedron Lett., 1982, 23, 4589;
25. D. J. S. Tsai and D. S. Matteson, Tetrahedron Lett., 1981, 22, 2751.
26. W. Bernhard and I. Fleming, J. Organomet. Chem., 1984, 271, 281.
27. G. Schmid and W. Hofheinz, J. Am. Chem. Soc., 1983, 105, 624;
28. I. Fleming and N. K. Terrett, J. Organomet. Chem., 1984, 264, 99.
29. E. Vogel, G. Caravatti, P. Franck, P. Aristoff, C. Moody, A.-M. Becker, D. Felix and A. Eschenmoser, Chem. Lett., 1987, 219.
30. A. Eschenmoser, personal communication.
31. Y. Ito, M. Nakatsuka and T. Saegusa, J. Am. Chem. Soc., 1982, 104, 7609.
32. S. Hoff, L. Brandsma, J. F. Arens, Red. Trav. Chim. Pays-Bos, 1968, 87, 916.
33. K. Furuta, M. Ishiguro, R. Haruta, N. Ikeda and H. Yamamoto, Bull. Chem. Soc. Jpn., 1984, 57, 2768, and reference cited therein;
34. C. C. Shen and C. Ainsworth, Tetrahedron Lett., 1979, 87.
35. J. Pornet, D. Mesnard and L. Miginiac, Tetrahedron Lett., 1982, 23, 4083.
36. H. M. Schmidt and J. F. Arens, Recl. Trav. Chim. Pays-Bas, 1967, 86, 1138.
37. H. Hommes, H. D. Verkruijsse and L. Brandsma, Recl. Trav. Chim. Pays-Bos, 1980, 99, 113.
38. J. W. Wilt and C. F. Dockus, J. Am. Chem. Soc., 1970, 92, 5813;
39. M. R. Smith, Jr. and H. Gilman, J. Organomet. Chem., 1972, 37, 35.
40. L. M. Harwood, Aldrichimica Acta, 1985, 18, 25.
41. The Aldrich Library of NMR Spectra, ed. C. J. Pouchert, 2nd ed., vol. 1, p. 1114D.
42. G. Höfle and W. Steglich, Synthesis, 1972, 619.
43. C. E. Bishop and G. W. Morrow, J. Org. Chem., 1983, 48, 657.
44. M. Furber, R. J. K. Taylor and S. C. Burford, J. Chem. Soc., Perkin Trans 1, 1986, 1809.
45. E. Vedejs and H. W. Fang, J. Org. Chem., 1984, 49, 210.
46. I. Fleming and I. Paterson, Synthesis, 1979, 736.
47. R. W. Saalfrank and M. Hanek, Tetrahedron, 1988, 44, 4787.
48. M. Miyashita, T. Yanami and A. Yoshikoshi, Org. Synth., 1990, Coll. Vol. VII, 396.
49. J. Tsuji, I. Shimizu and K. Yamamoto, Tetrahedron Lett., 1976, 2975;
50. E. Nakamura, K. Hashimoto and I. Kuwajima, J. Org. Chem., 1977, 42, 4166;
51. I. Kuwajima and I. Azegami, Tetrahedron Lett., 1979, 2369.
52. Y. Ito, Y. Amino, M. Nakatsuka and T. Saegusa, J. Am. Chem. Soc., 1983, 105, 1586.
53. A. I. Meyers and K. Lutomski, J. Org. Chem., 1979, 44, 4464.
54. M. Evers, L. Christiaens, G. Llabres and M. Baiwir, Magn. Reson. Chem, 1987, 25, 1018
55. (Chem. Abstr., 1988, 109, 72 891h).
56. I. C. Nordin, J. Heterocycl. Chem., 1966, 3, 531.
57. L. I. Krimen, Org. Synth., 1988, Coll. Vol. VI, 8.
58. A. K. Bose, B. Lal, W. A. Hoffmann III and M. S. Manhas, Tetrahedron Lett., 1973, 1619.
59. J. Besançon, S. Top, J. Tirouflet, B. Gautheron and Y. Dusausoy, J. Organomet. Chem., 1975, 94, 35;
60. Y. Dusausoy, J. Protas, J. Besançon and S. Top, J. Organomet. Chem., 1975, 94, 47.
61. B. B. Elsner, H. E. Strauss and E. J. Forbes, J. Chem. Soc., 1957, 578.
62. BP 681 990; (Chem. Abstr., 1954, 48, P4585);
63. T. Mitsui, M. Kitahara and T. Nagase, J. Sci. Res. Inst. Tokyo, 1956, 50, 65
64. (Chem. Abstr., 1957, 51, 8658f).