First thermal and transition metal catalysed intramolecular [4+2] cycloaddition reactions with N-tethered ynamides

Synlett

Volumn , Issue 5, 2003, Pages 708-710

  Witulski, Bernhard ^a   Lumtscher, Jan ^a   Bergsträßer, Uwe ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Alkynyliodonium salts; Catalysis; Diels Alder reaction; Tetrahydroindoles; Ynamides

Indexed keywords

INDOLE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; ELECTRON; PROTON TRANSPORT; ROOM TEMPERATURE; SYNTHESIS; THERMAL ANALYSIS;

EID: 0037267658     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38357     Document Type: Article

References (47)

1. (a) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650.
2. (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. E. Angew. Chem. Int. Ed. 2002, 41, 1701.
3. (c) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction; Wiley and Sons: Chichester, 2002.
4. (a) Fearnley, S. P.; Market, E. Chem. Commun. 2002, 438.
5. (b) Padwa, A.; Bur, S. K.; Danca, D. M.; Ginn, J. D.; Lynch, S. M. Synlett 2002, 851.
6. (c) Oppolzer, W.; Flaskamp, E.; Bieber, L. W. Helv. Chim. Acta 2001, 84, 141.
7. (d) Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120.
8. (e) Magnus, P.; Cairns, P. M. J. Am. Chem. Soc. 1986, 108, 217.
9. (f) Martin, S. F.; Tu, C.; Kimura, M.; Simonsen, S. H. J. Org. Chem. 1982, 47, 3634.
10. (g) Stork, G.; Morgans, D. J. Jr. J. Am. Chem. Soc. 1979, 101, 7110.
11. (a) Genet, J. P.; Ficini, J. Tetrahedron Lett. 1979, 1499.
12. (b) Iwamoto, K.; Fukuta, H.; Suzuki, S.; Maruyama, J.; Oishi, E.; Miyashita, A.; Higashino, T. Heterocycles 1996, 43, 2409.
13. (c) Barluenga, J.; Ferrero, M.; Peláez-Arango, E.; López-Ortiz, F.; Palacios, F. J. Chem. Soc., Chem. Commun. 1994, 865.
14. (d) Padwa, A.; Gareau, Y.; Harrison, B.; Rodriguez, A. J. Org. Chem. 1992, 57, 3540.
15. (e) Boger, D. L.; Dang, Q. Tetrahedron 1988, 44, 3379.
16. (f) Himbert, G.; Brunn, W. Liebigs Ann. Chem. 1986, 1067.
17. (g) For Hetero Diels-Alder reactions with ynamines, see: van Elburg, P. A.; Honig, G. W. N.; Reinhout, D. N. Tetrahedron Lett. 1987, 28, 6397.
18. (h) See also: Vilsmaier, E.; Baumheier, R. Chem. Ber. 1989, 122, 1285.
19. Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 498.
20. (a) Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281.
21. (b) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965.
22. (c) Witulski, B.; Buschmann, N.; Bergstäßer, U. Tetrahedron 2000, 56, 8473.
23. (d) Witulski, B.; Gößmann, M. Synlett 2000, 1793.
24. (e) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1999, 38, 2426.
25. (f) Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879.
26. (g) For other contributions to the chemistry of ynamides, see: Hoffmann, R. W.; Brückner, D. New J. Chem. 2001, 25, 369.
27. (h) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
28. (i) Mulder, J, A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
29. (j) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
30. (k) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 809.
31. (a) Kitamura, T.; Kotani, M.; Yokoyama, T.; Fujiwara, Y.; Hori, K. J. Org. Chem. 1999, 64, 680.
32. (b) Murch, P.; Arif, A. M.; Stang, P. J. J. Org. Chem. 1997, 62, 5959.
33. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
34. Feldman, K. S.; Mareska, D. A. J. Am. Chem. Soc. 1998, 120, 4027.
35. 3): δ = 144.7, 136.6, 133.8, 130.0, 129.8, 127.6, 134.6, 116.3, 75.8, 59.5, 50.6, 30.9, 21.6.
36. Nickel(0)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824. (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) DiMauro, E. F.; Kozlowski, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 439.
37. Nickel(0)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824. (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) DiMauro, E. F.; Kozlowski, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 439.
38. Nickel(0)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824. (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) DiMauro, E. F.; Kozlowski, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 439.
39. Nickel(0)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432. (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824. (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255. (d) DiMauro, E. F.; Kozlowski, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 439.
40. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
41. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
42. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
43. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
44. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
45. Rhodium(I)- and cationic rhodium(I)-catalysed intramolecular [4+2] cycloaddition reactions: (a) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. (c) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145. (d) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443. (e) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077. (f) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
46. 3) δ = 143.5, 134.6, 131.8, 129.5, 128.5, 127.8, 125.7, 124.8, 47.9, 36.8, 32.0, 31.0, 29.6, 29.4, 22.9, 21.5, 14.0.
47. -3. Data were collected on a STOE-IPDS at r.t., the structure was solved by direct methods using SHELXS-97 and refined using SHELXL-97. CCDC: 194177.