W(CO5)(L)-catalyzed construction of cyclic carbon frameworks

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 60, Issue 11 SPEC., 2002, Pages 1036-1048

  Iwasawa, Nobuharu ^a   Kusama, Hiroyuki ^a   Maeyama, Katsuya ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; COMPLEXATION; ELECTROCHEMISTRY; ETHERS; IODINE COMPOUNDS; ISOMERIZATION; KETONES; NAPHTHALENE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNE; BENZOPYRANYLIDENE COMPLEXES; DIELS-ALDER REACTION; ELECTROCYCLIZATION; POLYCYCLIC COMPOUND; SILYL ENOL ETHER; VINYLIDENE;

TUNGSTEN COMPOUNDS;

EID: 0036879687     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.60.1036     Document Type: Article

References (71)

1. Szymanska-Buzar, T.; Downs, A. J.; Greene, T. M.; Marshall, A. S. J. Organomet. Chem. 1995, 495, 163.
2. For the review of vinylidene complexes, see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
3. (b) Bruce, M. I. Swincer, G. A. Adv. Organomet. Chem. 1983, 22, 59.
4. For recent examples for the synthetic use of vinylidene intermediates of group 6 metals, see: (c) Parlier, A.; Rudler, H. J. Chem. Soc., Chem. Commun. 1986, 514.
5. (d) Quayle, P.; Rahman, S.; Herbert, J. Tetrahedron Lett. 1995, 36, 8087.
6. (e) Cosset, C.; Del Río, I.; Péron, V.; Windmüller, B.; Le Bozec, H. Synlett 1996, 435.
7. (f) Ohe, K.; Yokoi, T.; Miki, K.; Nishino, F.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 526.
8. For synthetic use of vinylidene or π-alkyne intermediates of other transition metals, see: (g) Trost, B. M. Chem. Ber. 1996, 129, 1313.
9. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507.
10. (i) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319.
11. (j) Ohe, K.; Kojima, M.; Yonehara, K.; Uemura, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1823.
12. (k) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 2867.
13. Landon, S. J.; Shulman, P. M.; Geoffroy, G. L. J. Am. Chem. Soc. 1985, 107, 6739.
14. Dötz, K. H.; Sturm, W. Organometallics, 1987, 6, 1424.
15. (a) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
16. (b) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687.
17. (c) McDonald, F. E.; Zhu, H. Y. H. Tetrahedron 1997, 53, 11061.
18. (d) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691.
19. (e) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
20. (f) McDonald, F. E. Chem. Eur. J. 1999, 5, 3103.
21. (a) Barrett, A. G. M.; Brock, C. P.; Sturgess, M. A. Organometallics, 1985, 4, 1903.
22. (b) Aumann, R.; Kuckert, E. Chem. Ber. 1987, 120, 1939.
23. Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928.
24. (a) Thebtaranonth, C.; Thebtaranonth, Y. "Cyclization Reactions", CRC Press, Boca Raton, 1994.
25. (b) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
26. (c) Grigg, R.; Sridharan, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds; Pergamon: Oxford, 1995; Vol 12, p 299.
27. (a) Albrecht, U.; Wartchow, R.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 910.
28. (b) Hoffmann, H. M. R.; Herden, U.; Breithor, M.; Rhode, O. Tetrahedron 1997, 53, 8383.
29. (c) Bruyere, D.; Gaignard, G.; Bouyssi, D.; Balme, G. Tetrahedron Lett. 1997, 38, 827.
30. (d) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339.
31. (e) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4081.
32. (f) Kim, K.; Okamoto, S.; Sato, F.; Org. Lett. 2001, 3, 67.
33. (g) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
34. For the reaction of transition metal-alkene or alkyne complexes with nucleophiles, see: (a) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds; Pergamon: Oxford, 1995; Vol 12, p 601.
35. (b) Hegedus, L. S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds; Pergamon: Oxford, 1991; Vol 4, p 571.
36. For the reactions of silyl enol ethers with alkenes promoted by palladium(II) complexes, see: (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494.
37. (b) Ito, Y.; Aoyama, H.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 4519.
38. (c) Kende, A. S.; Roth, B.; Sanfilippo, P. J. J. Am. Chem. Soc. 1982, 104, 1784.
39. (d) Kende, A. S.; Roth, B.; Sanfillippo, P. J.; Blacklock, T. J. J. Am. Chem. Soc. 1982, 104, 5808. Recently, the cyclization reaction of ω-alkenyl-1,3-diketone was reported by the catalytic use of palladium complex; see: ref 9g.
40. For the reactions of silyl enol ethers with alkynes promoted by mercury (II) compounds, see: (a) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
41. (b) Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773.
42. (c) Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 5746.
43. (d) Frontier, A. J.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 6686.
44. Conia, J. M.; Le Perchec, P. Synthesis 1975, 1.
45. Iwasawa, N.; Maeyama, K.; Kusama, H. Org. Lett. 2001, 3, 3871.
46. (a) Negishi, E.; Tour, J. M. Tetrahedron Lett. 1986, 27, 4869.
47. (b) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1991, 56, 5544.
48. (c) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genêt, J.-P. Tetrahedron Lett. 1996, 37, 2003.
49. Kusama, H.; Yamabe, H.; Iwasawa, N. Org. Lett. 2002, 4, 2569.
50. Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344.
51. In 1996, Merlic et al. reported the first example of the transition metal-catalyzed electrocyclization of dienynes via ruthenium vinylidene intermediates. See, ref 2i. See also, Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809.
52. Iwasawa, N.; Shido, M.; Maeyama, K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226.
53. For a general review, see: Okamura, W. H.; de Lera, A. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp 699-750.
54. Synthesis of an isomeric benzo[e]pyranylidene complex was reported using the aldol-type reaction of a methyl carbene complex with salicylaldehyde; however, synthesis of benzo[d]pyranylidene complexes of group 6 metals has not been reported before: (a) Aumann, R.; Heinen, H. Chem. Ber. 1987, 120, 537.
55. (b) Licandro, E.; Maiorana, S.; Papagni, A.; Zanotti, G. A.; Cariati, F.; Bruni, S.; Moret, M.; Chiesi V. A. Inorg. Chim. Acta 1994, 220, 233.
56. Several methods have been reported for the synthesis of pyranylidene complexes. For examples, see: (a) Aumann, R.; Meyer, A. G.; Fröhlich, R. J. Am. Chem. Soc. 1996, 118, 10853.
57. (b) Ohe, K.; Miki, K.; Yokoi, T.; Nishino, F.; Uemura, S. Organometallics 2000, 19, 5525.
58. (c) Miki, K.; Yokoi, T.; Nishino, F.; Ohe, K.; Uemura, S. J. Organomet. Chem. 2002, 645, 228.
59. Professor Berke and his coworkers have mentioned in one of their papers the possibility of the formation of a benzopyranylidene complex by electrocyclization of the vinylidene intermediate which is produced by the dimerization of propiolate on reaction with a chromium carbonyl complex. However, they have proposed this possibility based only on the observation that the color of the solution of this vinylidene complex changed depending on the polarity of the solvent, and they neither detected nor isolated the pyranylidene complex at all. See: Berke H.; Härter, P.; Huttner, G.; Zsolnai, L. Z. Naturforsh. 1981, 36b, 929.
60. Wulff et al. have reported that electron-rich olefins react with pyranylidene complexes to give dihydrobenzene derivatives. However, their reactivity is not very high, the dienophiles are usually employed as solvent, and it takes a long time for completion of the reaction. Wang, S. L. B.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. Aumann et al. have also reported the same type of reactions using a stoichiometric amount of enamines as dienophiles. See, ref 22a.
61. Kusama, H.; Shiozawa, F.; Shido, M.; Iwasawa, N. Chem. Lett. 2002, 124.
62. Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199.
63. Similar reactions of benzopyranones normally require high reaction temperature or an acid catalyst. For the Diels-Alder reaction of pyrone derivatives, see: (a) Jones, D. W.; Thompson, A. M. J. Chem. Soc., Perkin Trans. 1 1993, 2533.
64. (b) Bleasdale, D. A.; Jones, D. W. J. Chem. Soc., Perkin Trans. 1 1991, 1683.
65. (c) Van Broeck, P. I.; Vanderzande, D. J.; Kiekens, E. G.; Hoornaert, G. J. J. Chem. Soc., Perkin Trans. 1 1991, 639.
66. (d) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.
67. (a) Kakehi, A.; Ito, S.; Mitani, M.; Kanaoka, M. Bull. Chem. Soc. Jpn. 1994, 67, 1646.
68. (b) Soni, R. R.; Trivedi, K. N. Indian J. Chem., Sect. B 1993, 32B, 991.
69. (c) Battye, P. J.; Jones, D. W. J. Chem. Soc., Perkin Trans. 1 1986, 1479.
70. d) Ciganek, E. Org. React. 1984, 32, 1.
71. (e) Fallis, A. G. Can. J. Chem. 1984, 62, 183.