Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 15, 1999, Pages 2143-2153

  Bedford, Simon B ^a   Bell, Kathryn E ^b   Bennett, Frank ^a   Hayes, Christopher J ^b   Knight, David W ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001544820     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902411e     Document Type: Article

References (64)

1. F. Bennett, D. W. Knight and G. Fenton, J. Chcm. Soc., Perkin Trans. A 1991, 133 and 1543.
2. S. B. Bedford, G. Fenton, D. W. Knight and D. E. Shaw, J. Chem. Soc., Perkin Trans, l, 1996, 1505.
3. P. A. Bartlett, D. P. Richardson and J. Myerson, Tetrahedron, 1984, 40,2317.
4. J. E. Baldwin, J. Chcm. Soc., Chem. Commun., 1976,734and 738; for a discussion of why 5-endo-trig cyclizations are particularly unfavourable, see
5. J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman and R. C. Thomas, J. Client. Soc., Client. Commun., 1976, 736.
6. D. R. Williams, J. Grote and Y. Harigaya, Tetrahedron Lett., 1984, 25, 5231.
7. See also D. R. Williams and F. H. White, J. Org. Chem., 1987, 52, 5067;
8. A. B. Reitz, S. O. Nortey B. E. MaryanofT, D. Liotta and R. Monahan, III, J. Org. Client., 1987, 52, 4191;
9. C. E. Tonn, J. M. Palazon, C. Ruiz-Pcrcz, M. L. Rodriguez and V. S. Martin, Tetrahedron Lett., 1988, 29, 3149.
10. P. A. Bartlett and J. Myerson, J. Am. Chem. Soc., 1978,100, 3950.
11. M. Srebnik and R. Mcchoulam, J. Chem. Soc., Client. Commun., 1984, 1070.
12. R. D. Evans, J. W. Magce and J. H. Schauble, Synthesis, 1988, 862.
13. S. Takano, V. Sekiguchi, Y. Shimazaki and K. Ogasawara, Tetrahedron Lett., 1989, 30, 4001.
14. F. Bennett, D. W. Knieht and G. Fcnton, J. Chem Soc.,Perkin Trans. 7,1991,519.
15. For a review, see P. A. Bartlett, Asymmetric Synthesis, vol. 3, ed. J. D. Morrison, Academic Press, New York, 1984, eh. 6.
16. M. J. Kurth, R. L. Beard, M. Olmstead and J. G. Macmillan, J. Am. Cliem.Soc., 1989,111,3712.
17. H. Günther, NMR Spectroscopy, 2nd edn., Georg Thieme Verlag, Stuttgart, 1992; English translation, John Wiley and Sons Ltd., Chichester, 1995.
18. H. Dehmlow, J. Mulzer, C. Seilz, A. R. Strecker and A. Kohlmann, Tetrahedron Lett., 1992, 33, 3607.
19. W. R. Kirner, J. Am. Cliem. Soc., 1926, 48, 2745;
20. J. Hine and P. B. Langford, J. Am. Chem. Soc., 1956, 78, 5002;
21. J. Hine, Physical Organic Chemistry, McGraw-Hill, New York, 1956.
22. W. H. Kruizinea, B. Strijtveen and R. M. Kellogg, J. Org. Chem., 1981,46,4321.
23. E. J. Corey, K. C. Nicolaou-and M. Shibasaki, J. Chem. Soc., diem. Commun., 1975, 658.
24. S. Saito, H. .Nakajima, M. Inaba and T. Moriwake, Tetrahedron Lett., 1989,30,837.
25. P. Galatsis and D. J. Parks, Tetrahedron Lett., 1994,35, 6611.
26. P. Galatsis, S. D. Miilan and G. Ferguson, J. Org. Chem., 1997, 62, 5048.
27. T. L. B. Boivin, Tetrahedron, 1987, 43, 3309;
28. J.-C. Harmange and B. Figadère, Tetrahedron: Asymmetry, 1993,4, 1711.
29. For a preliminary communication, see S. B. Bedford, K. E. Bell, G. Fenton, C. J. Hayes, D. W. Knieht and D. Shaw, Tetrahedron Lett., 1992,33, 6511.
30. K. Chibale and S. Warren, J. Chem. Soc., Perkin Trans, l, 1996, 1935;
31. J. Eames and S. Warren, Tetrahedron Lett., 1996, 37, 3525;
32. J. Eames, M. A. de las Heras and S. Warren, Tetrahedron Lett., 1996, 37, 4077;
33. J. Eames, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996,37,4823.
34. For a review, see S. R. Harring, E. D. Edstrom and T. Livinghouse, Adr. Heterocycl. Nat. Prod. Synth., 1992, 2, 299.
35. B. H. Lipshutzand J. C. Barton, J. Am. Client. Soc., 1992,114,1084;
36. E. D. Mihelich and G. A. Hite, J. Am. Chem. Soc., 1992, 114, 318,
37. but see J. M. Barks, D. W. Knight, C. J. Seaman and G. G. Weingarten, Tetrahedron Lett., 1994,35,7259.
38. B. Lipshutz and T. Gross, J. Org. Chem., 1995, 60, 3572.
39. S. H. Kang and S. B. Lee, Tetrahedron Lett., 1993, 34, 1955 and 7579.
40. D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1998,39, 8909.
41. M. E. Jung and C. J. Nichols, Tetrahedron Lett., 1996,37, 7667.
42. J. M. Barks, D. W. Knight and G. G. Weingarten, J. Chem. Soc.. Chem. Commun., 1994, 719.
43. Y. Landais, D. Planchenault and V. Weber, Tetrahedron Lett., 1995, 36, 2987;
44. O. Andrey, L. Ducry, Y. Landais, D. Planchenault and V. Weber, Tetrahedron, 1997,53,4338.
45. K. C. Nicolaou, S. P. Seitz, W. J. Sipio and J. F. Blount, J. Am. Chcm. Soc., 1979,101, 3884;
46. K. C. Nicolaou, Tetrahedron, 1981,37,4097.
47. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915;
48. A. D. Jones, D. W. Knieht, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 1999,40, 3267.
49. D. P. Perrin, W. L. F. Armarego and D. R. Perrin, Purification of Laboratory Chemicals, Pergamon Press, Oxford, 2nd edn., 1985.
50. A. Alexakis and D. Jachiet, Tetrahedron, 1989,45, 6197.
51. M. Yamaguchi and I. Hirao, Tetrahedron Lett., 1983, 24, 391.
52. K. L. Mikolajczak and C. R. Smith, Jr., J. Org. Chcm., 1978, 43, 4762.
53. R. E. Ireland and J. A. Marshall, J. Am. Chem. Soc., 1959, 81, 2907;
54. R. A. Houghten, R. A. Simpson, R. N. Hanson and H. Rapoport, J. Org. Chem., 1979,44,4536.
55. H. H. Meyer, Annakn, 1984, 977;
56. F. Bennett, G. Fenton and D. W. Knight, Tetrahedron, 1994,50, 5147.
57. S. Henrot, M. Larchevêque and Y. Petit, Synth. Commun., 1986, 16, 183; M. Larchevêque and S. Henrot, Tetrahedron, 1990, 46, 4277.
58. E. Hungerbiihler, R. Naef, D. Wasmuth, D. Scebach, H.-R. Loosli and A. Wehrli, Ifelr. Chim. Ada, 1980,63, 1960.
59. M. Fetizon and M. Jurion, J. Client. Soc., Citent. Commun., 1972, 382.
60. B. O'Conner and G. Just, Tetrahedron Lett., 1987, 28, 3235.
61. Cf. L. W. Butz, E. W. Butz and A. M. Gaddis, J. Org. Chcm., 1940,5, 171.
62. T. Nakai and K. Mikami, Org. React. (N.Y.), 1994, 46, 105 and references cited therein.
63. R. Kaiser, Der. Food Sci., 1988, 18, 669.
64. B. E. Rossiter and K. B. Sharpless, J. Org, Chcm., 1984,49, 3707.