Ring-Closing Metathesis and Related Processes in Organic Synthesis

Accounts of Chemical Research

Volumn 28, Issue 11, 1995, Pages 446-452

  Grubbs, Robert H ^a   Miller, Scott J ^a   Fu, Gregory C ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542763298     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00059a002     Document Type: Article

References (64)

1. Feldman, J.; Schrock, R. R. Prog. Inorg. Chem. 1991, 39, 1-74.
2. Grubbs, R. H.; Turnas, W. Science 1989, 243, 907-915.
3. Ivin, K. J. Olefin Metathesis; Academic: New York, 1983.
4. Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter.
5. Trost, B. M.; Trost, B. K. J. Am. Chem. Soc. 1991, 113, 1850-1852.
6. Trost, B. M.; Trost, B. K. Tetrahedron Lett. 1991, 32, 3647-3650.
7. Herrison, J. L.; Chauvin, Y. Makromol. Chem. 1970, 141, 161-176.
8. Kupper, W.; Streck, R. Chem.-Ztg. 1975, 99, 464.
9. Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855-856.
10. Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843-862.
11. Schrock, R. R.; Krouse, S. A.; Knoll, K.; Feldman, J.; Murdzek, J. S.; Yang, D. C. J. Mol. Catal. 1988, 46, 243-253.
12. Quignard, F.; Leconte, M.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1985, 1816-1817.
13. Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 21, 2955-2958.
14. Warwel, S.; Katzker, H.; Rauenbusch, C. Angew. Chem., Int. Ed. Engl. 1987, 26, 702-703.
15. Toreki, R.; Schrock, R. R. J. Am. Chem. Soc. 1990, 112, 2449-2451.
16. Toreki, R.; Schrock, R. R.; Davis, W. M. J. Am. Chem. Soc. 1992, 114, 3367-3380.
17. Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
18. Bazan, G. C.; Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378-8387.
19. Bazan, G. C.; Oskam, J. H.; Cho, H.-N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899-6907.
20. Belen'kii, L. I. In Advances in Heterocyclic Chemistry;, Katritzky, A. R, Ed.; Academic: New York, 1988; Vol. 44, Chapter 4.
21. Comprehensive Heterocyclic Chemistry;, Meth-Cohn, O., Ed.; Pergamon: New York, 1984.
22. Bogolepova, E. I.; Fridman, R. A.; Bashkirov, A. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 27, 2429.
23. Levisalles, J.; Rudler, H.; Villemin, D. J. J. Organomet. Chem. 1979, 164, 251-257.
24. In intermolecular cases employing highly reactive W-based catalysts, the competing β-elimination has been observed: Hillmyer, M. A.; Grubbs, R. H. Macromolecules 1993, 26, 872-874.
25. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426-5427.
26. Forbes, M. D. E.; Patton, J. T.; Myers, T. L.; Maynard, H. D.; Smith, W. D., Jr.; Schulz, G. R.; Wagener, K. B. J. Am. Chem. Soc. 1992, 114, 10978-10980.
27. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
28. The Alkaloids: Chemistry and Pharmacology; Brossi, A., Cordell, G. A., Eds.; Academic: New York, 1992.
29. Alkaloids: Chemical and Biological Perspectives;, Pelletier, S. W., Eds.; Wiley-Interscience: New York, 1988.
30. Related problems had been encountered in studies concerning the metal alkylidene mediated dimerization of β-unsaturated esters. Feldman, J.; Murdzek, J. S.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 2260-2265.
31. Martin, S. F.; Liao, Y.; Chen, H. J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008.
32. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
33. Schrock, R. R.; DePue, R. T.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423-1435.
34. Schrock, R. R.; DePue, R. T.; Feldman, J.; Yap, K. B.; Yang, D. C.; Davis, W. M.; Park, L.; DiMare, M.; Schofield, M.; Anhaus, J.; Walborsky, E.; Evitt, E.; Kruger, C.; Betz, P. Organometallics 1990, 9, 2262-2275.
35. Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
36. Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 960.
37. Novak, B. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 7542.
38. McGrath, D. V.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 3611-3613.
39. Binger, P.; Muller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610-611.
40. Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130-8145.
41. Flatt, B. T.; Grubbs, R. H.; Blanski, R. L.; Calabrese, J. C.; Feldman, J. Organometallics 1994, 13, 2728-2732.
42. Li, R. T.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 10032-10040.
43. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
44. Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
45. Grubbs, R. H. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 1829-1833.
46. Wu, Z.; Benedicto, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975-4977.
47. Lynn, D.; Kanaoka, S.; Grubbs, R. H. Submitted to Macromolecules.
48. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
49. Sita has recently applied RCM employing 1 to the synthesis of a cyclopentene monomer: Sita, L. R. Macromolecules 1995, 28, 656-657.
50. Chen, Z.-R.; Claverie, J. P.; Grubbs, R. H.; Kornfield, J. A. Macromolecules 1995, 28, 2147-2154.
51. Miller, S. J.; Kim, S. H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
52. Professor S. F. Martin has employed the Mo-based alkylidene 1 to a related cyclization in studies directed toward the total synthesis of FR900482. Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169-1170.
53. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856.
54. Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737-738.
55. Kim, S. H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801-10802.
56. Recently a related report on enyne metathesis employing catalyst 3 has appeared: Kinoshita, A.; Mori, M. Synlett 1994, 1020-1022.
57. Martin, S. F.; Liao, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694.
58. Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194.
59. Houri, A. F.; Xu, Z.; Cogan, D.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2844-2943.
60. Descotes, G.; Ramza, J.; Basset, J. M.; Pagano, S. Tetrahedron Lett. 1994, 35, 7379-7382.
61. Nugent, W. A.; Feldman, J.; Calabrese, J. C. J. Am. Chem. Soc. 1995, 117, 8992-8998. W. A., Feldman, J., and Calabrese, J. C.
62. Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124.
63. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int., Ed. Engl., in press.
64. Catalysts 1 and 4b are commercially available from Strem Chemicals, Inc.