Stereocontrolled synthesis of E-homoallylic sulfides with 1,4,5 related chiral centres using the [2,3] sigmatropic rearrangement of sulfonium ylides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1996, Pages 359-376

  Hartley, Richard C ^a   Richards, Ian C ^b   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b AgrEvo UK Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542503337     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000359     Document Type: Article

References (53)

1. R. C. Hartley, S. Warren and I. C. Richards, Tetrahedron Lett., 1992, 33, 8155.
2. R. C. Hartley, S. Warren and I. C. Richards, J. Chem. Soc., Perkin Trans. 1, 1994, 507.
3. R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1979, 18, 563;
4. I. E. Marko, in Comprehensive' Organic Synthesis, ed. B. M. Trost, I. Fleming and G. Pattenden, Pergamon Press, Oxford, 1990, vol. 3, ch. 3.10.
5. For example: P. A. Grieco, J. Org. Chem., 1973, 38, 2572;
6. G. M. Blackburn and W. D. Ollis, J. Chem. Soc., Chem. Commun., 1968,
7. 1261; S. Julia, C. Huyn and V. Ratovelomanana, Bull. Soc. Chim. Fr., 1977, 710.
8. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.
9. E. Vedejs, Acc. Chem. Res., 1984, 17, 358;
10. V. Ceré, C. Paolucci, E. Sandri and A. Fava, J. Org. Chem., 1981, 46, 3315;
11. V. Ceré, C. Paolucci, E. Sandri and A. Fava, J. Org. Chem., 1979, 44, 4128;
12. V. Ceré, C. Paolucci, E. Sandri and A. Fava, J. Org. Chem., 1978, 43, 4826.
13. V. K. Aggarwal and S. Warren, Tetrahedron Lett., 1987, 28, 1925;
14. V. K. Aggarwal and S. Warren, Tetrahedron Lett., 1986, 27, 101.
15. M. Ballestra, J. Kallmerton and M. D. Wittman, Tetrahedron Lett., 1988, 29, 6905;
16. T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885;
17. Y. Yamamoto, J. Oda and Y. Inouye, J. Org. Chem., 1976, 41, 303.
18. E. Vedejs and M. J. Mullins, J. Org. Chem., 1979, 44, 2947;
19. M. Yoshimoto, S. Ishara, E. Nakayama and N. Soma, Tetrahedron Lett., 1972, 13, 2923.
20. Z. Kosarych and T. Cohen, Tetrahedron Lett., 1982, 23, 3019.
21. R. S. Garigipati, R. Cordova, M. Parvez and S. M. Weinreb, Tetrahedron, 1986, 42, 2979.
22. B. M. Trost and R. F. Hammen, J. Am. Chem. Soc., 1973, 95, 962;
23. S. H. Tahir, M. M. Olmstead and M. J. Kurth, Tetrahedron Lett., 1991, 32, 335;
24. M. J. Kurth, S. H. Tahir and M. M. Olmstead, J. Org. Chem., 1990, 55, 2286.
25. P. C. Cagle, A. M. Arif and J. A. Gladysz, J. Am. Chem. Soc., 1994, 116, 3655.
26. F. Kido, Y. Kawada, M. Kato and A. Yoshikoshi, J. Chem. Soc., Chem. Commun., 1994, 32, 789 and ref. 1 therein;
27. S. Mageswaran, W. D. Ollis and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1981, 1953;
28. E. Vedejs and M. J. Mullins, J. Org. Chem., 1979, 44, 2947.
29. K. Kondo and I. Ojima, J. Chem. Soc., Chem. Commun., 1972, 62;
30. R. W. Case, A. M. Davies, W. D. Ollis, C. Smith and I. O. Sutherland, J. Chem. Soc., Chem. Commun., 1969, 293.
31. V. K. Aggarwal, I. Coldham, S. McIntyre and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 451.
32. Y. D. Wu and K. N. Houk, J. Org. Chem., 1991, 56, 5657.
33. A. de Groot and B. J. M. Jansen, Tetrahedron Lett., 1981, 22, 887;
34. A. de Groot and B. J. M. Jansen, Synthesis, 1985, 434.
35. C. H. Heathcock, in Asymmetric Synthesis, ed. J. D. Morrison, Academic, Orlando, 1984, vol. 3, p. 111.
36. K. Chibale, R. C. Hartley, K. Jenkins, M. Simons, S. Warren and I. C. Richards. Tetrahedron Lett., 1993, 34, 6783.
37. Compare this to the smooth lactonisation observed with imides: K. Chibale and S. Warren, Tetrahedron Lett., 1992, 33, 4369.
38. F. H. Salisbury and S. Warren, Tetrahedron Lett., 1992, 33, 539;
39. F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 3425;
40. S. McIntyre and S. Warren, Tetrahedron Lett., 1990, 31, 3457;
41. V. K. Aggarwal, I. Coldham, S. McIntyre, F. H. Sansbury, M. J. Villa and S. Warren, Tetrahedron Lett., 1988, 29, 4885.
42. A. Merz, Angew. Chem., Int. Ed. Engl., 1973, 12, 846.
43. S. Czernecki, C. Georgoulis and C. Provelenghiou, Tetrahedron Lett., 1976, 17, 3535.
44. C. H. Heathcock, M. C. Pirrung, S. H. Montgomery and J. Lampe, Tetrahedron, 1981, 37, 4087.
45. W. R. Roush, J. Org. Chem., 1991, 56, 4151.
46. K. Chibale and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1995, 2411;
47. V. K. Aggarwal, Ph.D. Thesis, University of Cambridge, 1986.
48. S. A. McIntyre, Ph.D. Thesis, University of Cambridge, 1988.
49. C. H. Behrens, S. Y. Ko, K. B. Sharpless and F. J. Walker, J. Org. Chem., 1985, 50, 5687.
50. A. Fischi and P. M. Muller, Helv. Chim. Acta, 1980, 63, 529.
51. D. H. Williams and I. Fleming, Spectroscopic Methods in Organic Chemistry, McGraw-Hill, London, 4th edn., 1987, p. 130.
52. L. Gattermann, Ber. Dtsch. Chem. Ges., 1889, 32, 1136;
53. J. Drabowicz and M. Mikolajcyzk, Synthesis, 1980, 33.