Chiral organometallic reagents. Part XXIII.1 On the stereochemistry of the carbolithiation reaction of vinyl sulfides

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 2, 1999, Pages 183-191

  Hoffmann, Reinhard W ^a   Koberstein, Ralf ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000985448     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808116f     Document Type: Article

References (69)

1. For part XXII of this series see: V. Schulze and R. W. Hoffmann, Chem. Eur. J., 1999, 5, 337.
2. L. R. Subramaniam, in Methoden der Organischen Chemie. (Houben-Weyl), ed. M. Hanack, Thieme, Stuttgart, vol. E19d. 1993, pp. 744-747.
3. R. Waack and M. A. Doran, J. Org. Chem., 1967, 32, 3395.
4. (a) For a review see: W. F. Bailey and T. V. Ovaska, Advances in Detailed Reaction Mechanisms. ed. J. M. Coxon, JAI Press. Greenwich CT, vol. 3, 1994, pp. 251-273: for further references:
5. (b) W. F. Bailey and X.-L. Jiang, J. Org. Chem., 1994, 59, 6528;
6. (c) M. P. Cooke Jr., J. Org. Chem., 1994, 59, 2930;
7. (d) I. Coldham and R. Hufton, Tetrahedron Lett., 1995, 36, 2157;
8. (e) I. Coldham and R. Hufton, Tetrahedron, 1996, 52, 12541;
9. (f) A. Krief, A. Nazih and M. Hobe, Tetrahedron Lett., 1995, 36, 8111;
10. (g) A. Krief, B. Kenda and B. Remacle, Tetrahedron Lett., 1995, 36, 7917;
11. (h) I. Coldham, R. Hufton and D. J. Snowden, J. Am. Chem. Soc., 1996, 118, 5322;
12. (i) E. Lorthiois, I. Marek and J. F. Normant, Tetrahedron Lett., 1996, 37, 6693;
13. (j) D. Zhang and L. Liebeskind, J. Org. Chem., 1996, 61, 2594;
14. (k) W. F. Bailey and E. R. Punzalan, Tetrahedron Lett., 1996, 37, 5435;
15. (l) W. F. Bailey, N. M. Wachter-Jurcsak, M. R. Pineau, T. V. Ovaska, R. R. Warren and C. E. Lewis, J. Org., Chem., 1996, 61, 8216;
16. (m) A. Krief and J. Bousbaa, Synlett, 1996, 1007;
17. (n) I. Coldham, R. Hufton and R. E. Rathmell, Tetrahedron Lett., 1997, 38, 7617;
18. (o) I. Coldham, M. M. S. Lang-Anderson, R. E. Rathmell and D. J. Snowden, Tetrahedron Lett., 1997, 38, 7621;
19. (p) M. J. Woltering, R. Fröhlich and D. Hoppe, Angew. Chem., 1997, 109, 1804; Angew. Chem., Int. Ed. Engl., 1997, 36, 1764;
20. (p) M. J. Woltering, R. Fröhlich and D. Hoppe, Angew. Chem., 1997, 109, 1804; Angew. Chem., Int. Ed. Engl., 1997, 36, 1764;
21. (q) M. P. Cooke and J.-J. Hiang, Synlett, 1997, 535;
22. (r) W. F. Bailey and Y. Tao, Tetrahedron Lett., 1997, 38, 6157;
23. (s) W. F. Bailey and M. W. Carson, Tetrahedron Lett., 1997, 38, 1329;
24. (t) A. Krief and J. Bousbaa, Tetrahedron Lett., 1997, 38, 6291;
25. (u) K. Tomooka, N. Komine and T. Nakai, Tetrahedron Lett., 1997, 38, 8939;
26. (v) X. Wei and R. J. K. Taylor, Tetrahedron Lett., 1997, 38, 6467;
27. (w) M. Oestreich, R. Fröhlich and D. Hoppe, Tetrahedron Lett., 1998, 39, 1745.
28. F. Chen, B. Mudryk and T. Cohen, Tetrahedron, 1994, 50, 12793.
29. W. F. Bailey, X.-L. Jiang and C. E. McLeod, J. Org. Chem., 1995, 60, 7791.
30. W. F. Bailey and X.-L. Jiang, J. Org. Chem., 1996, 61, 2596.
31. W. F. Bailey, J. J. Patricia and T. T. Nurmi, Tetrahedron Lett., 1986, 27, 1865.
32. W. F. Bailey, A. D. Khanolkar, K. Gavaskar, T. V. Ovaska, K. Rossi, Y. Thiel and K. B. Wiberg, J. Am. Chem. Soc., 1991, 113, 5720.
33. X. Wei and R. J. K. Taylor, Chem Commun., 1996, 187.
34. P. F. Hudrlik and D. Peterson, J. Am. Chem. Soc., 1975, 97, 1464.
35. W. E. Parham and R. F. Motter, J. Am. Chem. Soc., 1959, 81, 2146.
36. D. J. Ager, Tetrahedron Lett., 1981, 22, 587.
37. W. R. Dolbier and Y. Chen, J. Org. Chem., 1992, 57, 1947.
38. S. Raucher and G. A. Koolpe, J. Org. Chem., 1978, 43, 4252.
39. W. F. Bailey and E. R. Punzalan, J. Am. Chem. Soc., 1994, 116, 6577.
40. T. Rölle and R. W. Hoffmann, J. Chem. Soc., Perkin Trans. 2, 1995, 1953.
41. (a) R. L. Funk, G. L. Bolton, K. M. Brummond, K. E. Ellestad and J. B. Stallman, J. Am. Chem. Soc., 1993, 115, 7023;
42. (b) S. Norsikian, J. Marek and J.-F. Normant, Tetrahedron Lett., 1997, 38, 7523;
43. (c) J. Barluenga, R. Sanz, A. Granados and F. J. Fananás, J. Am. Chem. Soc., 1998, 120, 4865.
44. B. Mudryk and T. Cohen, J. Am. Chem. Soc., 1993, 115, 3855.
45. (a) G. W. Klumpp, Recl. Trav. Chim. Pays-Bas. 1986, 105, 1;
46. (b) B. Mudryk and T. Cohen, J. Org. Chem., 1991, 56, 5761;
47. (c) R. F. Schmitz, F. J.-J. de Kanter, M. Schakel and G. W. Klumpp, Tetrahedron, 1994, 50, 5933.
48. A. Krief, D. Derouane and W. Dumont, Synlett, 1992, 907.
49. W. Oppolzer, Angew. Chem., 1989, 101, 39: Angew. Chem., Int. Ed. Engl., 1989, 28, 38.
50. W. Oppolzer, Angew. Chem., 1989, 101, 39: Angew. Chem., Int. Ed. Engl., 1989, 28, 38.
51. A. Krief, B. Kenda and B. Remacle, Tetrahedron, 1996, 52, 7435.
52. (a) P. G. McDougal, B. D. Condon, M. D. Laffosse Jr., A. M. Lauro and D. VanDerveer, Tetrahedron Lett., 1988, 29, 2547;
53. (b) T. Kato, S. Marumoto, T. Sato and I. Kuwajima, Synlett, 1990, 671;
54. (c) H. J. Reich and M. D. Bowe, J. Am. Chem. Soc., 1990, 112, 8994;
55. (d) G. P. Lutz, A. P. Wallin, S. T. Kerrick and P. Beak, J. Org. Chem., 1991, 56, 4938;
56. (e) F. Wang, J. Tang, L. Labaudinière, I. Marek and J. F. Normant, Synlett, 1995, 723;
57. (f) T. Shimozuka, Y. Kikori, M. Asaoka and H. Takei, J. Chem. Soc., Perkin Trans. 1, 1996, 119.
58. R. W. Hoffmann, R. K. Dress, T. Ruhland and A. Wenzel, Chem. Ber., 1995, 128, 861.
59. R. W. Hoffmann, R. Koberstein, B. Remacle and A. Krief, Chem. Commun., 1997, 2189.
60. M. P. Heitz, A. Wagner and C. Mioskowski, J. Org. Chem., 1989, 54, 500.
61. S. T. Kabanyane and D. I. MaGee, Can. J. Chem., 1992, 70, 2758.
62. T. Mandai, M. Ueda, K. Kashiwagi, M. Kawada and J. Tsuji, Tetrahedron Lett., 1993, 34, 111.
63. H. C. Stiasny and R. W. Hoffmann, Chem. Eur. J., 1995, 1, 619.
64. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.
65. H. J. Reich and K. J. Kulicke, J. Am. Chem. Soc., 1995, 117, 6621.
66. R. K. Dress, T. Rölle and R. W. Hoffmann, Chem. Ber., 1995, 128, 673: and references quoted.
67. R. D. Evans, J. W. Magee and J. H. Schauble, Synthesis, 1988, 862.
68. H. J. R. de Boer, O. S. Akkerman and F. Bickelhaupt, Angew. Chem., 1988, 100, 735: Angew. Chem., Int. Ed. Engl., 1988, 27, 687.
69. H. J. R. de Boer, O. S. Akkerman and F. Bickelhaupt, Angew. Chem., 1988, 100, 735: Angew. Chem., Int. Ed. Engl., 1988, 27, 687.