Recent advances in olefin metathesis and its application in organic synthesis

Tetrahedron

Volumn 54, Issue 18, 1998, Pages 4413-4450

  Grubbs, Robert H ^a   Chang, Sukbok ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE;

CATALYSIS; CYCLIZATION; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032580376     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10427-6     Document Type: Review

References (117)

1. 1. (a) Grubbs, R. H. and Pine, S. H. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Paquette, L. A. Eds.; Pergamon: New York, 1991, Vol. 5, Chapter 9.3.
2. (b) Schrock, R. R. in The Strem Chemiker, Vol. XIV, Strem Chemicals, Newburgport, 1992, No. 1, p. 1-6.
3. (c) Ivin, K. J. and Mol, J. C. Olefin Metathesis and Metathesis Polymerization, Academic Press, San Diego, 1997.
4. 2. (a) Herrison, J. L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161-176.
5. (b) Sehrer, J. C.; Gundiah, S. J. Sci. Ind. Res. 1983, 55, 250.
6. (c) Kress, J.; Osborn, J. A.; Greene, R. M. E.; Ivin, K. J.; Rooney, J. J. J. Chem. Soc., Chem. Commun. 1985, 874-876.
7. (d) Kress, J.; Osborn, J. A.; Greene, R. M. E.; Ivin, K. J.; Rooney, J. J. J. Am. Chem. Soc. 1987, 109, 899-901.
8. 3. (a) Noshay, A. and McGrath, J. E. Block Coploymers, Academic, New York, 1977.
9. (b) Novak, B. M.; Risse, W.; Grubbs, R. H. Adv. Polymer. Sci. 1992, 102, 47.
10. 4. (a) Warwel, S.; Siekermann, V. Makromol. Chem., Rapid Commun. 1983, 4, 423.
11. (b) Leymet, I.; Siove, A.; Parlier, A.; Rudler, H.; Fontanille, M. Makromol. Chem. 1989, 190, 2397.
12. (c) Liaw, D.-J.; Lin, C.-L. J. Polymer Sci., A, Polymer Chem. 1993, 31, 3151.
13. 5. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
14. (b) 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.
15. (c) Bazan, G. C.; Oskam, J. H.; Cho, H.-N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899-6907.
16. 6. (a) Nguyen, S. T.; Jonson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974-3975.
17. (b) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
18. (c) Wu, Z.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 5503-5511.
19. 7. Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195-200.
20. 8. (a) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317-4325.
21. (b) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784-790.
22. 9. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2197-2181. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041.
23. 9. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2197-2181. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041.
24. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
25. 10. For an initial report considering the functional group tolerance, see: Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
26. 11. For detailed mechanism and activity of the catalyst 3 type, see: Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
27. 12. Couturier, J.-L.; Paillet, C.; Leconte, M.; Basset, J.-M.; Weiss, K. Angew. Chem. Int. Ed. Engl. 1992, 31, 628-631.
28. 13. (a) Couturier, J.-L.; Tanaka, K.; Leconte, M.; Basset, J.-M.; Ollivier, J. Angew. Chem. Int. Ed. Engl. 1993, 32, 112-115.
29. (b) Couturier, J.-M.; Leconte, M.; Basset, J.-M. J. Organomet. Chem. 1993, 451, C7-C9.
30. 14. Leconte, M.; Pagano, S.; Mutch, A.; Lefebvre, F.; Basset, J. M. Bull. Soc. Chim. Fr. 1995, 132, 1069-1071.
31. 15. Nugent, W. A.; Feldman, J.; Calabrese, J. C. J. Am. Chem. Soc. 1995, 117, 8992-8998.
32. 2 derivatives were previously employed as catalysts for ring-opening metathesis polymerization, see: Bell, A. J. Mol. Catal. 1992, 76, 165-180.
33. 4 per tungsten complex afforded reaction rates ca. one half of those obtained with 2 equiv.
34. 18. For another example of the use of olefin metathesis (using the catalyst 5) in the synthesis of a carbocyclic nucleosides, see: Martinez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 67, 7963-7966.
35. 19. For some examples, see: (a) Wallace, K. C.; Liu, A. H.; Dewan, J. C.; Schrock, R. R. J. Am. Chem. Soc. 1988, 110, 4964-4977.
36. (b) Toreki, R.; Vaughan, G. A.; Schrock, R. R.; Davis, W. M. J. Am. Chem. Soc. 1993, 115, 127-137.
37. (c) Johnson, L. K.; Frey, M.; Ulibarri, T. A.; Virgil, S. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 8167-8177.
38. (d) Schatternmann, F. J.; Schrock, R. R.; Davis, W. M. J. Am. Chem. Soc. 1996, 778, 3295-3296.
39. 20. Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 21, 2955-2958.
40. 21. For recent reviews, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552.
41. (b) Schmalz, H.-G. Angew. Chem. Int. Eng. Ed. 1995, 34, 1833-1836.
42. (c) Hashimi, A. S. K. J. prakt. Chem. 1997, 339, 195-199.
43. 22. (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426-5427.
44. (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
45. (c) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
46. 23. Kirkland, T.; Grubbs, R. H. J. Org. Chem. in press.
47. 24. Shon, Y.-S.; Lee, T. R. Tetrahedron Lett. 1997, 38, 1283-1286.
48. 25. Similar results was previously reported, see: Armstrong, S. K.; Christie, B. A. Tetrahedron Lett. 1996, 37, 9373-9376.
49. 26. Maier, M. E.; Langenbacher, D.; Rebien, F. Liebigs Ann. 1995, 1843-1848.
50. 27. Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192-4193.
51. 28. Dyatkin, A. B. Tetrahedron Lett. 1997, 38, 2065-2066.
52. 29. Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550.
53. 30. This slowly reacting diene 19 was used since the routes for the preparation of the di-terminal olefin substrate gave unsatisfactory yields.
54. 31. Chang, S.; Grubbs, R. H. J. Org. Chem. in press.
55. 32. Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760.
56. 33. (a) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298.
57. (b) Heron, N. M.; Adams, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 6205-6206.
58. 34. (a) Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
59. (b) Linderman, R. J.; Siedlecki, J.; O'Neil, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919-6920.
60. 35. Hölder, S.; Blechert, S. Synlett 1996, 505-506.
61. 36. Irreversible oxygenation of the catalyst was assumed to be a main reason for the low yields.
62. 37. For a precedent example for the formation of cyclic enol ether using RCM, see: Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
63. 38. (a) Nicolaou, K. C.; Postema, M. H. D.; Claiborne, C. F. J. Am. Chem. Soc. 1996, 118, 1565-1566.
64. (b) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
65. 39. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 123-126.
66. 40. Clark, J. S.; Kettle, J. G. Tetrahedron Lett. 1997, 38, 127-130.
67. 41. Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem. Int. Eng. Ed. 1996, 35, 2376-2378.
68. 42. Huwe, C. M.; Blechert, S. Synthesis 1997, 61-67.
69. 43. Fujimure, O.; de la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865-1871.
70. 44. Fujimure, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499-2500.
71. 45. Rutjes, F. P. J. T.; Shoemaker, H. E. Tetrahedron Lett. 1997, 38, 677-680.
72. 46. Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Commun., 1996, 2231-2232.
73. 47. Barrett, A. G. M.; Baugh, S. P. D.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A. Chem. Commun., 1997, 155-156.
74. 48. Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 2309-2322.
75. 49. Hammer, K.; Undheim, K. Tetrahedron 1997, 55, 5925-5936.
76. 50. Garro-Hélion, F.; Guibé, F. Chem. Commun., 1996, 641-642.
77. 51. Clark, T. D.; Ghadiri, M. R. J. Am. Chem, Soc. 1995, 117, 12364-12365.
78. 52. Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856.
79. 53. Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
80. 54. Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943.
81. 55. Fürstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008.
82. 56. McKervey, M. A.; Pitarch, M. Chem. Commun., 1996, 1689-1690.
83. 57. Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601-2604.
84. 58. Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944.
85. 59. Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
86. 60. Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. Int. Eng. Ed. 1996, 55, 2399-2401.
87. 61. Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168.
88. 62. Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 523-524.
89. 63. Taylor, R. E.; Haley, J. D. Tetrahedron Lett. 1997, 38, 2061-2064.
90. 64. Meng, D.; Su, D.-S.; Balog, A.; Bertinato, P.; Sorenson, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. J. Am. Chem. Soc. 1997, 119, 2733-2734.
91. 65. Marsella, M.; Maynard, H.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1101-1103.
92. 66. For precedent example of crown ether formation by RCM, see: König, B.; Horn, C. Synlett 1996, 1013-1014.
93. 67. Mohr, B.; Week, M.; Sauvage, J.-P.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1997, 36, 1308-1310.
94. 68. Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640.
95. 69. Kim, S.-R; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801-10802.
96. 70. Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
97. 71. Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356-8357.
98. 72. Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. manuscript in prepration.
99. 73. Coates, G. W.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 229-230.
100. 74. Schuster, M.; Pernerstorfer. J.; Blechert, S. Angew. Chem. Int. Eng. Ed. 1996, 35, 1979-1980.
101. 75. Peters, J.-U.; Blechert, S. Synlett, 1997, 348-350.
102. 76. van Maarseveen, J. H.; den Hartog, J. A. J.; Engelen, V.; Finner, E.; Visser, G.; Kruse, C. G. Tetrahedron Lett. 1996, 37, 8249-8252.
103. 77. Nicolaou, K. V.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourioumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272.
104. 78. Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488-1489.
105. 79. For early report of selective cross metathesis with styrenes, see: Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
106. 80. Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162-5163.
107. 81. Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120.
108. 82. Feng, J.; Schuster, M.; Blechert, S. Syntett, 1997, 129-130.
109. 83. Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun., 1997, 1107-1108.
110. 84. Brümmer, O.; Rückert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446.
111. 85. Schuster, M.; Lucas, N.; Blechert, S. Chem. Commun., 1997, 823-824.
112. 86. Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106-5109.
113. 87. Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 257-259.
114. 88. Schneider, M. F.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 411-412.
115. 89. For a precedent example, see: Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
116. 90. Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478-1479.
117. 91. Tallarico, J. A.; Bonitatebus, P. P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.