Palladium-catalyzed cross-coupling reactions of arylmetal compounds with β-substituted α-iodoenones and a cyclohexyl triflate

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9485-9498

  Boße, Folkert ^a   Tunoori, Ashok Rao ^a   Niestroj, André J ^a   Gronwald, Oliver ^a   Maier, Martin E ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; CYCLOHEXANE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0011810136     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00489-9     Document Type: Article

References (51)

1. 1. Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem. 1995, 107, 819-845; Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
2. 1. Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem. 1995, 107, 819-845; Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
3. 2. For reviews, see: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416.
4. 2. For reviews, see: a) Nicolaou, K. C.; Dai, W.-M. Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416.
5. b) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235-243.
6. c) Nicolaou, K. C.; Smith, A L. Acc. Chem. Res. 1992, 25, 497-503.
7. d) Nicolaou, K. C; Smith, A. L.; Yue, E. W. Proc. Natl. Acad. Sci. USA 1993, 90, 5881-5888.
8. e) Skrydstrup, T.; Audrain, H.; Ulibarri, G.; Grierson, D. S. in Recent Progress in the Chemical Synthesis of Antibiotics, G. Lukacs Ed., Springer-Verlag, 1993, Vol 2, pp. 213-292.
9. f) Maier, M. E. Synlett 1995, 13-26.
10. 3. a) Konishi, M.; Ohkuma, H.; Matsumoto, K.; Saitoh, K.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1991, 44, 1300-1305.
11. b) Kamei, H.; Nishiyama, Y.; Takahashi, A.; Obi, Y.; Oki, T. J. Antibiot. 1991, 44, 1306-1311.
12. c) Miyoshi-Saitoh, M.; Morisaki, N.; Tokiwa, Y.; Iwasaki, S.; Konishi, M.; Saitoh, K.; Oki, T. J. Antibiot. 1991, 44, 1037-1044.
13. d) Shiomi, K.; Iinuma, H.; Naganawa, H.; Hamada, M.; Hattori, S.; Nakamura, H.; Takeuchi, T.; Iitaka, Y. J. Antibiot. 1990, 43, 1000-1005.
14. e) Sugiura, Y.; Shiraki, T.; Konishi, M.; Oki, T. Proc. Natl. Acad Sci. U. S. A. 1990, 87, 3831-3835.
15. f) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3715-3716.
16. g) Konishi, M.; Ohkuma, H.; Matsumoto, K.; Tsuno, T.; Kamei, H.; Miyaki, T.; Oki, T.; Kawaguchi, H. J. Antibiot. 1989, 42, 1449-1452.
17. 4. Total syntheses: a) Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43.
18. b) Shair, M. D.; Yoon, T.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1883-1885; Angew. Chem. Int. Ed. Engl. 1995, 34, 1721-17-23.
19. b) Shair, M. D.; Yoon, T.; Danishefsky, S. J. Angew. Chem. 1995, 107, 1883-1885; Angew. Chem. Int. Ed. Engl. 1995, 34, 1721-17-23.
20. 5. Maier, M. E.; Abel, U. Synlett 1995, 38-40.
21. 6. Tietze, F.; Eicher, T. Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Georg Thieme Verlag, Stuttgart, 2nd ed. 1991, 118.
22. 7. Quesada, M. L.; Schlessinger, R. H. Synth. Commun. 1976, 6, 555.
23. 8. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287-290.
24. 9. a) Sawyer, J. S.; Kucerovy, A., Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842-853.
25. b) Johnson, C. R.; Medich, J. R. J. Org. Chem. 1988, 53, 4131-4133.
26. 10. Knochel, P.; Chou, T.-S.; Jubert, C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588-599.
27. 11. Webster, F. X.; Silverstein, R. M. Synthesis 1987, 922-924.
28. 12. a) Shing, T. K. M.; Tang, Y. Tetrahedron 1990, 46, 6575-6584.
29. b) Shing, T. K. M.; Tang, Y. Tetrahedron 1991, 47, 4571-4578.
30. c) Ulibarri, G.; Nadler, W.; Skrydstrup, T.; Audrain, H.; Chiaroni, A.; Riche, C.; Grierson, D. J. Org. Chem. 1995, 60, 2753-2761.
31. 13. a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
32. b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552.
33. 14. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
34. 15. Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1273-1277.
35. 16. Pearson, A. J.; Richards, I. C.; Gardner, D. V. J. Org. Chem. 1984, 49, 3887-3891.
36. 17. Dupré, B.; Meyers, A. I. J. Org. Chem. 1991, 56, 3197-3198.
37. 18. Myers, A. G.; Fraley, M. E.; Tom, N. J. J. Am. Chem. Soc. 1994, 116, 11556-11557.
38. 19. Negishi, E.; Owczarczyk, Z. R.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4453-4456.
39. 20. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919-922.
40. 21. Nishikawa, T.; Isobe, M. Tetrahedron 1994, 50, 5621-5632.
41. 22. a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558.
42. b) Brown, J. M.; Pearson, M.; Jastrzebski, J. T. B. H.; Van Koten, G. J. Chem. Soc., Chem. Commun. 1992, 1440-1441.
43. 23. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253-266.
44. 24. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
45. 25. a) Segall, Y.; Granoth, I. J. Am. Chem. Soc. 1978, 100, 5130-5134.
46. b) see also: Hermann, W. A.; Broßmer, C.; Öfele, K.; Reisinnger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
47. b) see also: Hermann, W. A.; Broßmer, C.; Öfele, K.; Reisinnger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
48. 26. a) Data, J. B.; Bennett, R. B. J. Med. Chem. 1961, 4, 324-333.
49. b) Kublak, G. G.; Confalone, P. N. Tetrahedron Lett. 1990, 31, 3845-3848.
50. 27. Ungnade, H. E.; Kein, H. J. Org. Chem. 1949, 14, 911-913.
51. 28. Barton, D. H. R.; Donelly, D. M. X.; Finet, J. P. Guiry, P. J. J. Chem. Soc. Perkin Trans I 1992, 11, 1365-1375.