Stereoselective [2 + 2 + 2] cocyclotrimerization of oxa-and azabenzonorbornadienes † with alkynes catalyzed by nickel complexes: First transition metal-mediated synthesis of isobenzofuran and isoindole precursors

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 2, 2000, Pages 195-203

  Sambaiah, Thota ^a   Huang, Daw Jen ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; TOLUENE;

ALKYNES;

OLEFINS;

EID: 0034695718     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907654i     Document Type: Article

References (67)

1. W. Friedrichsen, Adv. Heterocycl. Chem., 1980, 26, 135;
2. B. Rickborn, Isobenzofurans in Advances in Theoretically Interesting Molecules, ed. R. P. Thummel, JAI Press, Greenwich, CT, 1989, vol. 1, eh. 1;
3. W. Friedrichsen, in Houben-Weyl, Methoden der Organischen Chemie, ed. R. Kreher, Thieme Verlag, Stuttgart, 1994, vol. E6b, pp. 163-216.
4. P. Vogel, D. Fattori, F. Gasparini and C. Le Drian, Synlett, 1990, 56, 2128;
5. P. Renaud and J.-P Vionnet, J. Org. Chem., 1993, 58, 5895;
6. T. A. Eggette, H. de Koning and H. O. Huisman, J. Chem. Soc., Perkin Trans, 1, 1978, 980;
7. G. Just and S. Kim, Tetrahedron Lett., 1976, 1063.
8. A. Padwa, C. O. Kappe and T. S. Reger, J. Org. Chem., 1996, 61, 4888.
9. A. Padwa, C. O. Kappe, J. E. Cochran and J. P. Snyder, J. Org. Chem., 1997, 62, 2786.
10. Y.-M. Man, T. C. W. Mak and H. N. C. Wong, J. Org. Chem., 1990, 55, 3214;
11. R. N. Warrener, D. N. Butler, W. Y. Liao, I. G. Pitt and R. A. Russsell, Tetrahedron Lett., 1991, 32, 1889;
12. H. Takeshita, A. Mori, S. Sugiyama and T. Tsuda, Bull. Chem. Soc. Jpn., 1986, 59, 3988;
13. C. W. Chan and H. N. C. Wong, J. Am. Chem. Soc., 1988, 110, 462;
14. K. Blatter and A.-D. Schlueter, Chem. Ber., 1989, 122, 1351;
15. H. Takeshita, Y. J. Yan, N. Kato, A. Mori and T. Nozoe, Tetrahedron Lett., 1995, 36, 5195;
16. R. N. Warrener, S. Wang, D. N. Butler and R. A. Russell, Synlett, 1997, 1, 44.
17. C. S. LeHoullier and G. W. Gribble, J. Org. Chem., 1983, 48, 1682;
18. J. R. Malpass, G. Sun, J. Fawcett and R. N. Warrener, Tetrahedron Lett., 1998, 39, 3083.
19. L. F. Fieser and M. J. Haddadin, J. Am. Chem. Soc., 1964, 86, 2081;
20. L. F. Fieser and M. J. Haddadin, Can. J. Chem., 1965, 43, 1599;
21. R. N. Warrener, J. Am. Chem. Soc., 1971, 93, 2346;
22. J. Luo and H. Hart, J. Org. Chem., 1989, 54, 1762;
23. S. E. Whitney, M. Winters and B. Rickborn, J. Org. Chem., 1990, 55, 929.
24. G. M. Priestley and R. N. Warrener, Tetrahedron Lett., 1972, 4295.
25. K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1984, 23, 539;
26. M. Lautens, W. Klute and W. Tam, Chem. Rev., 1996, 96, 49;
27. I. Ojima, M. Tzamarioudaki, Z. Li and R. J. Donovan, Chem. Rev., 1996, 96, 635.
28. S. H. Lecker, N. H. Nguen and K. P. C. Vollhardt, J. Am. Chem. Soc., 1986, 108, 856;
29. E. Negishi, L. S. Harring, Z. Owczarczyk, M. M. Mohamud and M. Ay, Tetrahedron Lett., 1992, 33, 3253;
30. H. E. Helson, K. P. C. Vollhardt and Z.-Y. Yang, Angew. Chem., Int. Ed. Engl., 1985, 24, 114;
31. R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691.
32. N. E. Schore, Chem. Rev., 1988, 88, 1081;
33. B. M. Trost, Science, 1996, 96,49.
34. A. J. Chalk, J. Am. Chem. Soc., 1972, 94, 5928;
35. H. Suzuki, K. Itoh, Y. Ishii, K. Simon and J. A. Ibers, J. Am. Chem. Soc., 1976, 98, 8494;
36. E. D. Sternberg and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 4841;
37. E. D. Sternberg and K. P. C. Vollhardt, J. Org. Chem., 1984, 49, 1574;
38. G. J. Balaich and I. P. Rothwell, J. Am. Chem. Soc., 1993, 115, 1581;
39. F. Slowinski, C. Aubert and M. Malacria, Tetrahedron Lett., 1999, 40, 707.
40. R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans, 1, 1988, 1365;
41. Z. Zhou, L. P. Battaglia, G. P. Chiusoli, M. Costa, M. Nardelli, C. Pelizzi and G. Predieri, J. Chem. Soc., Chem. Commun., 1990, 1632;
42. Z. Zhou, M. Costa and G. P. Chiusoli, J. Chem. Soc., Perkin Trans, 1, 1992, 1399;
43. Y. Yamamoto, H. Kitahara, R. Ogawa and K. Itoh, J. Org. Chem., 1998, 63, 9610.
44. T.-Y. Hsiao, K. C. Santhosh, K.-F. Liou and C.-H. Cheng, J. Am. Chem. Soc., 1998, 120, 12232.
45. T. Sambaiah, L.-P. Li, D.-J. Huang, C.-H. Lin, D. K. Rayabarapu and C.-H. Cheng, J. Org. Chem., 1999, 64, 3663.
46. S. Ikeda, N. Mori and Y. Sato, J. Am. Chem. Soc., 1997, 119, 4779;
47. S. Ikeda, H. Watanabe and Y. Sato, J. Org. Chem., 1998, 63, 7026;
48. N. Mori, S. Ikeda and Y. Sato, J. Am. Chem. Soc., 1999, 121, 2722.
49. For preliminary communication see: D.-J. Huang, T. Sambaiah and C.-H. Cheng, New J. Chem., 1998, 22, 1147.
50. C. D. Smith, J. Am. Chem. Soc., 1966, 88, 4273;
51. J. Meinwald, J. C. Meinwald and T. N. Baker, J. Am. Chem. Soc., 1964, 86, 4074.
52. T. Tsuda, S. Morikawa, R. Sumiya and T. Saegusa, J. Org. Chem., 1988, 53, 3140;
53. T. Tsuda, R. Sumiya and T. Saegusa, Synth. Commun., 1987, 17, 147.
54. D.-J. Huang and C.-H. Cheng, J. Organomet. Chem., 1995, 490, C1.
55. J. J. Eisch and J. E. Galle, J. Organomet. Chem., 1975, 96, C23;
56. J. J. Eisch, A. M. Piotrowski, K. I. Han, C. Kruger and Y. H. Tsay, Organometallics, 1985, 4, 224.
57. For production of a cobaltacyclopentadiene complex, see: Y. Wakatsuki, O. Nomura, K. Kitaura, K. Morokuma and H. Yamazaki, J. Am. Chem Soc., 1983, 105, 1907.
58. D. R. McAlister, J. E. Bercaw and R. G. Bergman, J. Am. Chem. Soc., 1977, 99, 1666.
59. For production of cobaltacyclopentene complex, see: Y. Wakatsuki, K. Aoki and H. Yamazaki, J. Am. Chem. Soc., 1974, 96, 5284;
60. Y. Wakatsuki, K. Aoki and H. Yamazaki, J. Am. Chem. Soc., 1979, 101, 123.
61. J.-P. Duan and C.-H. Cheng, Tetrahedron Lett., 1993, 34, 4019;
62. J.-P. Duan and C.-H. Cheng, Organometallics, 1995, 14, 1608;
63. C.-C. Feng, M. Nandi, T. Sambaiah and C.-H. Cheng, J. Org. Chem., 1999, 64, 3538.
64. L. S. Hegedus, in Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, California, 1994, ch. 8, pp. 248-255.
65. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Plenum Press, New York, 1991;
66. H. M. Colquhoun, J. Holton, D. J. Thompson and M. V. Twigg, New Pathways For Organic Synthesis-Practical Applications of Transition Metals, Plenum Press, New York, 1988.
67. G. M. L. Cragg, R. G. F. Giles and G. H. P. Roos, J. Chem. Soc., Perkin Trans, 1, 1975, 1339.