Ruthenium-catalyzed cyclizations of dienylalkynes via vinylidene intermediates

Journal of the American Chemical Society

Volumn 118, Issue 45, 1996, Pages 11319-11320

  Merlic, Craig A ^a   Pauly, Malinda E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029860625     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962684+     Document Type: Article

References (26)

1. For general reviews, see: (a) 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.
2. (b) Marvell, E. N. Thermal Electrocyclic Reactions', Academic: New York, 1980.
3. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon Press: New York, 1991; Vol. 5.
4. (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 7418.
5. (b) Merlic, C. A.; Xu, D.; Gladstone, B. G. J. Org. Chem. 1991, 58, 538.
6. For leading references, see: (a) Turnbull, P.; Heilman, M. J.; Moore, H. W. J. Org. Chem. 1996, 61, 2584.
7. (b) Koo, S. H.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389.
8. For a leading reference, see: Danheiser, R. L.; Casebier, D. S.; Firooznia, F. J. Org. Chem. 1995, 60, 8341.
9. (a) Merlic, C. A.; Burns, E. E.; Daqiang, X.; Chan, S. Y. J. Am. Chem. Soc. 1992, 114, 8722.
10. (b) Merlic, C. A.; Burns, E. E. Tetrahedron Lett. 1993, 34, 5401.
11. Saito, T.; Nakane, M.; Miyazaki, T.; Motoki, S. J. Chem. Soc., Perkin Trans, l 1989, 2140.
12. Bums, E. E. Ph.D. Dissertation, University of California, Los Angeles, CA, 1995.
13. For a review, see: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197.
14. For reviews, see: (a) Bruce, M. I.; Swincer, A. G. Organomet. Chem. 1983,22,59.
15. (b) Bruce, M. I. Chem. Rev. 1991,91, 197.
16. Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
17. Wang and Finn recently reported a diradical cycloaromatization reaction, stoichiometric in ruthenium, involving a vinylidene intermediate: Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 777, 8045.
18. For synthesis of complexes, see: (a) Brace, M. I.; Hameister, C.; Swincer, A. G.; Wallis, R. C. Inorg. Synth. 1982, 78.
19. (b) Ashby, G. S.; Bruce, M. I.; Tomkins, I.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1003.
20. Zelonka, R. A.; Baird, M. C. Can. J. Chem. 1972, 50, 3063.
21. Bennett, M. A.; Huang. T. N.; Matheson, T. W.; Smith, A. K. Inorg. Synth. 1982, 27, 74.
22. (e) Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
23. See also: (a) Cundari, T. R.; Gordon, M. S. J. Am. Chem. Soc. 1992, 114, 539.
24. (b) Bruce, M. I.; Swincer, A. G. Aust. J. Chem. 1980, 33, 1471.
25. Bozec, H. L; Ouzzine, K.; Dixneuf, P. H. Organometalucs 1991, 70, 2768.
26. Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chein. Soc. 1994, 116, 8105.