Alkynyliodonium salts in organic synthesis. Preparation of annelated dihydropyrroles by cascade addition/bicyclization of dienyltosylamide anions with phenyl(propynyl)iodonium triflate

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5650-5660

  Feldman, Ken S ^a   Mareska, David A ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNYL GROUP; ANION; BICYCLO COMPOUND; ISOPRENE; PYRROLE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CYCLIZATION; ISOMERISM; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033597803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9907538     Document Type: Article

References (51)

1. (a) Feldman, K. S.; Mareska, D. A.; J. Am. Chem. Soc. 1998, 120, 4027.
2. (b) Feldman, K. S.; Mareska, D. A. Tetrahedron Lett. 1998, 39, 4781.
3. Kirmse, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1164.
4. (b) Stang, P. J. Chem. Rev. 1978, 78, 333.
5. (a) Ervin, K. M.; Ho, J.; Lineberger, W. C. J. Phys. Chem. 1989, 91, 5974.
6. (b) Bodor, N.; Dewar, M. J. S.; Wasson, J. S. J. Am. Chem. Soc. 1972, 94, 9095.
7. Gallo, M. M.; Hamilton, J. P.; Schaeffer, H. F. III J. Am. Chem. Soc. 1990, 112, 8714.
8. Gilbert, J. C.; Giamalva, D. H. J. Org. Chem. 1992, 57, 4185.
9. Seyferth, D.; Mui, J. Y. P.; Damrauer, R. J. Am. Chem. Soc. 1968, 90, 6182.
10. (a) Stang, P. J.; Zhdankin, V. V. Tetrahedron 1998, 54, 10927.
11. (b) Stang, P. J. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 1995.
12. Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251.
13. (a) Köbrich, G.; Heinemann, H. J. Chem. Soc., Chem. Commun. 1969, 493.
14. (b) Köbrich, G.; Baumann, M. Angew. Chem., Int. Ed. Engl. 1972, 11, 52.
15. (a) Salinero, R. F.; Berson, J. A. Tetrahedron Lett. 1982, 23, 1447.
16. (b) Salinero, R. F.; Berson, J. A. J. Am. Chem. Soc. 1979, 101, 7094.
17. Chesick, J. P. J. Am. Chem. Soc. 1963, 85, 220.
18. (a) Little, R. D. Chem. Rev. 1996, 96, 93.
19. (b) Little, R. D. Chem. Rev. 1986, 86, 875.
20. (a) Billups, W. E.; Leavell, K. H.; Lewis, E. S.; Vanderpool, S. J. Am. Chem. Soc. 1973, 95, 8096.
21. (b) Kende, A. S.; Riecki, E. E. J. Am. Chem. Soc. 1972, 94, 1397.
22. (c) Roth, W. R.; Schmidt, T. Tetrahedron Lett. 1971, 3639.
23. (d) Pikulin, S.; Berson, J. A. J. Am. Chem. Soc. 1986, 107, 8274.
24. (e) Shields, T. C.; Billups, W. E.; Lepley, A. R. J. Am. Chem. Soc. 1968, 90, 4749.
25. (f) Gilbert, J. C.; Higley, D. P. Tetrahedron Lett. 1973, 2075.
26. Direct (IR) detection of triplet-4-methylene-2-pentene-1,5-diyl: Maier, G.; Senger, S. J. Am. Chem. Soc. 1997, 119, 5852.
27. (a) Davidson, E. R.; Gajewski, J. J.; Shook, C. A.; Cohen, T. J. Am. Chem. Soc. 1995, 33, 8495.
28. (b) Shook, C. A.; Romberger, M. L.; Jung, S.-H.; Xiao, M.; Sherbine, J. P.; Zhang, B.; Lin, F.-T.; Cohen, T. J. Am. Chem. Soc. 1993, 115, 10754.
29. Tsunoda, T.; Yamamoto, H.; Goda, K.; Ito, S. Tetrahedron Lett. 1996, 37, 2457.
30. Connell, R. D.; Helquist, P.; Akermark, B. J. Org. Chem. 1989, 54, 3359.
31. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
32. Wolinski, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745.
33. Davies, H. M. L.; Houser, J. H.; Thornley, C. J. Org. Chem. 1995, 60, 7529.
34. (a) Weber, W.; de Meijere, A. Chem. Ber. 1985, 118, 2450.
35. (b) Arora, S.; Binger, P.; Köster, R. Synthesis 1973, 146.
36. (c) Vincens, M.; Dumont, C.; Vidal, M. Can. J. Chem. 1979, 57, 2314.
37. (d) Akhachinskaya, T. V.; Shapiro, I. O.; Donskaya, N. A.; Shabarov, Y. S.; Shatenshtein, A. I. J. Org. Chem. USSR 1985, 21, 421.
38. (e) Akhachinskaya, T. V.; Donskaya, N. A.; Grishin, Y. K.; Shabarov, Y. S. J. Org. Chem. USSR 1987, 23, 295.
39. (f) Petasis, N. A.; Bzowej, E. I. Tetrahedron Lett. 1993, 43, 943.
40. (g) Ullman, E. F.; Fanshawe, W. J. J. Am. Chem. Soc. 1961, 83, 2379.
41. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
42. Boyd, J.; Epstein, W.; Fráter, G. J. Chem. Soc., Chem. Commun. 1976, 380.
43. Chou, W.-N.; White, J. B. Tetrahedron Lett. 1991, 32, 7637.
44. Ishii, Y.; Gao, C.; Xu, W.-X.; Iwasaki, M.; Hidai, M. J. Org. Chem. 1993, 58, 6818.
45. Huang, Y.; Shen, Y.; Zheng, J.; Zhang, S. Synthesis 1985, 57.
46. Myrboh, B.; Asokan, C. V.; Ila, H.; Junjappa, H. Synthesis 1984, 50.
47. Lu, X.; Huang, X.; Ma, S. Tetrahedron Lett. 1992, 33, 2535.
48. Riley, R. G.; Silverstein, R. M.; Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1974, 39, 1957.
49. Closa, M.; de March, P.; Figueredo, M.; Font, J.; Soria, A. Tetrahedron 1997, 53, 16803.
50. Zhdankin, V. V.; Scheuller, M. C.; Stang, P. J. Tetrahedron Lett. 1993, 34, 6853-6856.
51. Sanghavi, N. M.; Parab, V. L.; Patravale, B. S. Patel, M. N. Synth. Commun. 1989, 19, 1499.