The intramolecular stille reaction

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1999, Pages 1235-1246

  Duncton, Matthew A J ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746403712     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808261h     Document Type: Article

References (87)

1. D. Milstein and J. K. Stille, J. Am. Chem. Soc., 1978,100,3636.
2. D. Milstein arid J. K. Stille, J. Am. Chem. Soc., 1979,101,4992.
3. For a review see J. K. Stille, Angew Chem., Im. Ed. Engl., 1986,25,508. See also V. Farina, V. Krishnamurphy and W. J. Scott, Organic Reactions, 50, 1997, John Wiley & Sons, New York, and references therein.
4. For other contemporaneous metal-catalysed coupling reactions see: E. Negishi, A. O. King and N. Okukado, J. Org Chem., 1977,42,1821 and references cited therein.
5. Metal-catalysed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, 1998.
6. For organomagnesium coupling see M. Kumada, Pure Appl. Chem., 1980,52,669.
7. For organozinc coupling see E. Erdik, Tetrahedron, 1992,48,9577.
8. For organoborane coupling (Suzuki reaction) see N. Miyaura and A. Suzuki, Chem. Rev., 1995,95,2457 and references cited therein.
9. For organosilane coupling see Y. Hatanaka and T. Hiyama, Synleti, 1991,845.
10. For an excellent discussion oi New perspectives in the cross-coupling reactions oforganostannanes,
11. see V. Farina, Pure Appl. Chem., 1996,68,73, and references therein.
12. For reviews of the Heck reaction see: A. de Meijere and F. E. Meyer, Angew. Chem., Im. Ed. Engl., 1995,33,2379;
13. S. E. Gibson and R. J. Middleton, Contemp. Org. Synth., 1996,3,447 and references therein.
14. K. Takai, K. Nitta and K. Utimoto, J. Am. Chem. Soc., 1986,108,7408.
15. A. S. Kende, K. Koch, G. Dorey, I. Kaldor and K. Liu, J. Am. Chem. Soc., 1993,115,9842.
16. M. B. Andrus, S. D. Lepore and T. M. Turner, J. Am. Chem. Soc., 1997,119.12159.
17. For carbometallation/halide quench see: T. Jyojima, M. Katohno, N. Miyamoto, M. Nakata, S. Matsumara and K. Toshimo, Tetrahedron Lett., 1993,39,6003, and references cited therein.
18. J. Schwartz and J. A. Labinger, Angew. Chem., Im. Ed. Engl, 1976,15,333. For the in situ generation of Schwartz's reagent see B. H. Lipshutz, R. Keil and E. L. Ellsworth, Tetrahedron Lett., 1990, 31, 7257.
19. K. C. Nicolaou, P. Bertinato, A. D. Piscopio, T. K. Chakraborty and N. Minowa, J. Chem. Soc., Chem. Commun., 1993,619.
20. M. Treilhou, A. Fauve, J.-R. Pougny, J.-C. Promé and H. Veschambre, J. Org. Chem., 1992,57,3203.
21. D. J. Critcher, S. Connolly and M. Wills, Tetrahedron Lett., 1995,36,3763.
22. B. H. Lipshutz, C. Lindsley and A. Bhandari, Tetrahedron Lett., 1994,35,4669.
23. V. Farina, S. R. Baker, D. A. Benigni, S. I. Hauck and C. Sapino, J. Org. Chem., 1990,55,5833.
24. M. Belén Cid and G. Pattenden, Synlett, 1998,540.
25. S. K. Steward and A. Whiting, Tetrahedron Lett., 1995,36,3929.
26. G. Stork and K. Zhao, Tetrahedron Lett., 1989,30,2173.
27. X. Zhang, and M. Schlosser, Tetrahedron Lett., 1993,3-1,1925.
28. A. S. Kende, K. Kawamura and R. J. De Vita, J. Am. Chem. Soc., 1990,112,4070.
29. K. C. Nicolaou, B. E. Marron, C. A. Veale, S. E. Webber and C. N. Serhan,./ Org. Chem., 1989,54,5527.
30. Y. Masuda, M. Hoshi and A. Arase, Bull. Chem. Soc. Jpn., 1992,65,3294.
31. P. W. Collins, A. F. Gasiecki, W. E. Perkins, G. W. Gullikson, R. G. Bianchi, S. W. Kramer, J. S. Ng, E. E. Yonan, L. Swenton, P. H. Jones and R. F. Bauer J. Mcd. Chem., 1990,33,2784.
32. M. M. Goodman, M.-P. Kung, G. W. Kabalka, H. F. Kung and R. Switzer.y Med. Chem., 1994,37,1535.
33. J. P. Férézou, M. Julia, Y. Li, L. W. Liu and A. Pancrazi, Synlett, 1991,53.
34. H. Ali, J. Rousseau, M. A. Ghaffari and J. E. van Lier, J. Med. Chem., 1991,34,854.
35. H. X. Zhang, F. Guibé and G. Balavoine, J. Org. Chem., 1990,55,1857.
36. C. D. J. Boden, G. Pattenden and T. Ye, J. Chem. Soc., Perkin Trans. 7, 1996,2417.
37. A. B. Smith, S. M. Condon, J. A. McCauley, J. L-. Leazer, J. W. Leahy and R. E. Malcczka, J. Am. Chem. Soc., 1995,117,5407.
38. S. Sharma and A. C. Oehlschlager, J. Org. Chem., 1989,54,5064 and references cited therein.
39. D. A. Entwistle, S. I. Jordan, J. Montgomery and G. Pattenden, J. Chem. Soc., Perkin Trans, l, 1996,1315.
40. S. Kim and K. H. Kim, Tetrahedron Lett., 1995,36,3725.
41. D. M. Hodgson, Tetrahedron Lett., 1992,33,5603.
42. D. M. Hodgson, L. T. Boulton and G. N. Maw, Tetrahedron Lett., 1994,35,2231.
43. D. M. Hodgson, L. T. Boulton and G. N. Maw, Synlett, 1995,267.
44. R. J. Boyce and G. Pattenden, Tetrahedron Lett., 1996,37,3501.
45. M. D. ChfTand S. G. Pyne, Tetrahedron Lett., 1995,36,763.
46. W. D. Wulff, G. A. Peterson, W. E. Bauta, K.-S. Chan, K. L. Faron, S. R. Gilbertson, R. W. Kaesler, D. C. Yang and C. K. Murray, J. Org. Chem., 1986,51,277.
47. A. G. M. Barrett, M. L. Boys and T. L. Boehm, J. Chem. Soc., Chem. Commun., 1994,1881.
48. E. J. Corey and T. M. Eckrich, Tetrahedron Lett., 1984,25,2419.
49. B. H. Lipshutz and R. Keil, Inorg. Chim. Acta, 1994,220,41.
50. B. H. Lipshutz, R. Keil'and J. C. Barton, Tetrahedron Lett., 1992,33,5861.
51. A. B. Smith, and G. R. Ott, J. Am. Chem. Soc. 1996,118,13095.
52. E. Piers, R. W. Friesen and B. A. Keay, J Chem. Soc., Chem. Commun., 1985,809.
53. E. Piers, R. W. Friesen and B. A. Keay, Tetrahedron, 1991,47,4555.
54. E. Piers, R. W. Friesen and S. J. Rettig, Can. J. Chem., 1992,70,1385.
55. E. Piers and R. W. Friesen, J. Org. Chem., 1986,51,3405.
56. E. Piers and R. W. Friesen, Can. J. Chem., 1992,70,1204.
57. E. Piers and Y.-F. Lu, J. Org. Chem., 1988,53,926.
58. J. C. Bradley and T. Durst, J. Org. Chem., 1991,56,5459.
59. M. Hirama, K. Fujiwara, K. Shigematu and Y. Fukazawa, J. Am. Chem. Soc., 1989,111,4120.
60. J. K. Stille and M. Tanaka, J. Am. Chem. Soc., 1987,109,3785.
61. A. Kalivretenos, J. K. Stille and L. S. Hegedus, J. Org. Chem., 1991,56,2883.
62. A. B. Smith III and G. R. Ott, J. Am. Chem. Soc. 1998,120,3935.
63. Y. Kim, R. A. Singer and E. M. Carreira, Angew. Chem. Im. Ed., 1998,37,1261.
64. A. B. Smith III, S. M. Condon, J. A. McCauley, J. L. Leazer, J. W. Leahy and R. E. Maleczka, Jr., J. Am. Chem. Soc. 1995,117,5407.
65. T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett., 1998,39,6007.
66. D. J. Critcher and G. Pattenden, Tetrahedron Lett., 1996,37,9107.
67. G. Pattenden and S. M. Thom, Synlett, 1993,215.
68. D. A. Entwistle, S. I. Jordan, J. Montgomery and G. Pattenden, Synthesis, 1998,603.
69. C. Boden and G. Pattenden, Synlett, 1994,181.
70. A. Casaschi, R. Grigg, J. M. Sansano, D. Wilson and J. Redpath, Tetrahedron Lett., 1996,37,4413.
71. D. F. Taber and Y. Wang, J. Am. Chem. Soc., 1997,119,22.
72. T. S. McDermott, A. A. Mortlock and C. H. Heathcock, J. Org. Chem., 1996,61,700.
73. H. Finch, N. A. Pegg and B. Evans, Tetrahedron Lett., 1993,34,8353.
74. P. Quayle, J. Wang and J. Xu, Tetrahedron Lett., 1998,39,485.
75. K. C. Nicolaou, T. K. Chakraborty, A. D. Piscopio, N. Minowa and P. Bertinato,./ Am. Chem. Soc., 1993,115,4419.
76. M. D. Shair, T. Yoon and S. J. Danishefsky, J. Org. Chem., 1994,59,3755; M. D. Shair, T. Yoon, and S. J. Danishefsky, Angew. Chem., Im. Ed. EngJ., 1995, 34, 1721.
77. For a similar approach to the 9-membered enediyne unit in neocarzinostatin chromophore see: H. Tanaka, H. Yamada, A. Matsuda and T. Takahashi, Synlett, 1997,381.
78. J. S. Panek and C. E. Masse, J. Org. Chem., 1997,62,8290; C. E. Masse, M. Yang, J. Solomon and J. S. Panek, J. Am. Chem. Soc., 1998, 120,4123.
79. J. K. Stille, H. Su, D. H. Hill, P. Schneider, M. Tanaka, D. L. Morrison and L. S. Hegedus, Organomelallics, 1991,10,1993.
80. A. C. Gyorkos, J. K. Stille and L. S. Hegedus, J. Am. Chem. Soc., 1990,112,8465.
81. J. E. Baldwin, R. M. Adlington and S. H. Ramcharitar, J. Chem. Soc., Chem. Commun., 1991,940.
82. J. E. Baldwin, R. M. Adlington and S. H. Ramcharitar, Tetrahedron Lett., 1992,48,2957.
83. R. M. Adlington, J. E. Baldwin, A. Gansäuer, W. McCoull and A. T. Russell, J. Chem. Soc., Perkin Trans, l, 1994,1697.
84. E. Piers and T. Wong, J. Org. Chem.; 1993,58,3609.
85. G. D. Allred and L. S. Liebeskind, J. Am. Chem. Soc., 1996,118,
86. SO I. Paterson and J. Man, Tetrahedron Lett., 1997,38,695; cf. B. W.
87. Dymock, P. J. Kocienski and J.-M. Pons, Synthesis, 1998,1655.