Ruthenium-Catalyzed Polycyclization Reactions

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4291-4298

  Zuercher, William J ^a   Scholl, Matthias ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001117364     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972279g     Document Type: Article

References (36)

1. (a) Teitze, L. F. Chem. Rev. 1996, 96, 115-136.
2. (b) Hudlicky, T. Chem. Rev. 1996, 96, 3-30.
3. Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley-Interscience: New York, 1992.
4. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159.
5. Johnson, W. S.; Wiedhaup, K.; Brady, S. F.; Olson, G. L. J. Am. Chem. Soc. 1974, 96, 3979-3984.
6. Ihara, M.; Makita, K.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1994, 59, 6008.
7. Takahashi, T.; Katouda, W.; Sakamoto, Y.; Tomida, S.; Yamada, H. Tetrahedron Lett. 1995, 36, 2273.
8. (a) Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1990, 112, 8590.
9. (b) Negishi, E. Pure Appl. Chem. 1992, 64, 323-334.
10. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438.
11. (a) Kim, S.-H.; Bowden, N. B.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801.
12. (b) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
13. Zuercher, W. J. ; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640.
14. Recent examples of RCM of α,ω-dienes: (a) Grubbs, R. H.; Chang, S. B. Tetrahedron 1997, 38, 4757-4760 and references therein, (b) General RCM: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. General olefin metathesis: Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic: San Diego, 1997.
15. Recent examples of RCM of α,ω-dienes: (a) Grubbs, R. H.; Chang, S. B. Tetrahedron 1997, 38, 4757-4760 and references therein, (b) General RCM: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. General olefin metathesis: Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic: San Diego, 1997.
16. Recent examples of RCM of α,ω-dienes: (a) Grubbs, R. H.; Chang, S. B. Tetrahedron 1997, 38, 4757-4760 and references therein, (b) General RCM: Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references therein. General olefin metathesis: Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic: San Diego, 1997.
17. A cascade of diene RCM reactions was employed in the quantitative RCM of poly(1,2-butadiene) to produce a cyclopentene-based polymer. Coates, G. W.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 230-231
18. (a) Synthesis: Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
19. (b) Mechanism and activity: Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
20. Propargyl chloride 3, rather than the tosylate, was isolated from the reaction of 2 with tosyl chloride.
21. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
22. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438.
23. (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021-4024.
24. (b) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3679.
25. Bäckvall, J.-E.; Byström, S. E.; Aslanian, R. Tetrahedron Lett. 1985, 26, 1749-1752.
26. Bäckvall, J.-E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
27. Compounds 4 and 5 have been protected as trialkylsilyl ethers. Cyclization proceeds without this protection, but the reaction rate is slowed dramatically, possibly due to intramolecular chelation.
28. The extra substituent on the disubstituted olefin is employed to increase the relative rate of metathesis at the monosubstituted "productive" olefln. When the reaction is conducted with an acyclic precursor containing two monosubstituted olefins, product formation is observed at a slower rate and to a lesser extent.
29. A related process involving carbene-acetylene metathesis, enyne metathesis ring-closure, has been reported utilizing tungsten and ruthenium carbene complexes, (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020. (c) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Similarly, carbene-acetylene metathesis allows for the recently reported rearrangement-cyclization of triynes to produce aromatics, an example of which is shown, (d) Peters, J. U.; Blechert, S. Chem. Commun. 1997, 1983.
30. A related process involving carbene-acetylene metathesis, enyne metathesis ring-closure, has been reported utilizing tungsten and ruthenium carbene complexes, (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020. (c) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Similarly, carbene-acetylene metathesis allows for the recently reported rearrangement-cyclization of triynes to produce aromatics, an example of which is shown, (d) Peters, J. U.; Blechert, S. Chem. Commun. 1997, 1983.
31. A related process involving carbene-acetylene metathesis, enyne metathesis ring-closure, has been reported utilizing tungsten and ruthenium carbene complexes, (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020. (c) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Similarly, carbene-acetylene metathesis allows for the recently reported rearrangement-cyclization of triynes to produce aromatics, an example of which is shown, (d) Peters, J. U.; Blechert, S. Chem. Commun. 1997, 1983.
32. A related process involving carbene-acetylene metathesis, enyne metathesis ring-closure, has been reported utilizing tungsten and ruthenium carbene complexes, (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020. (c) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. Similarly, carbene-acetylene metathesis allows for the recently reported rearrangement-cyclization of triynes to produce aromatics, an example of which is shown, (d) Peters, J. U.; Blechert, S. Chem. Commun. 1997, 1983.
33. Although olefin substitution results only in a 4% increase in yield of 31 (Table 2, entries 1 and 2), the workup is greatly simplified due to the absence of difficult to separate impurities.
34. Chang, S.; Jones, L., II; Wang, C.; Henling, L. M.; Grubbs, R. H.; Organometallics 1997, submitted for publication.
35. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
36. Korach, M.; Nielsen, D. R.; Rideout, W. H. J. Am. Chem. Soc. 1960, 82, 4328.