A general model for selectivity in olefin cross metathesis

Journal of the American Chemical Society

Volumn 125, Issue 37, 2003, Pages 11360-11370

  Chatterjee, Arnab K ^a   Choi, Tae Lim ^a   Sanders, Daniel P ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS METATHESIS (CM);

FEEDSTOCKS; STOICHIOMETRY; STYRENE;

OLEFINS;

ALKENE; ALLYL ALCOHOL; STYRENE;

ARTICLE; CHEMICAL REACTION; CROSS METATHESIS; DIMERIZATION; MOLECULAR MODEL; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

ALKENES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0043194171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0214882     Document Type: Article

References (53)

1. (a) Scholl, S.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
2. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
3. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039; Angew. Chem. 1995, 107, 2179.
4. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039; Angew. Chem. 1995, 107, 2179.
5. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
6. (c) Belderrain, T. R.; Grubbs, R. H. Organometallics 1997, 16, 4001.
7. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
8. (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.
9. (c) Bazan, G. C.; Oskam, J, H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899.
10. For a recent review, see: Frenzel, U.; Nuyken, O. J. Polym Sci. Part A: Polym. Chem. 2002, 40, 2895.
11. (a) Fürstner, A. Angew. Chem. 2000, 112, 3013; Angew. Chem., Int. Ed. 2000, 39, 3140.
12. (a) Fürstner, A. Angew. Chem. 2000, 112, 3013; Angew. Chem., Int. Ed. 2000, 39, 3140.
13. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
14. (c) Kotha, S.; Sreenivasachary, N. Ind. J. Chem. B, 2001, 40, 763.
15. (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751.
16. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
17. (c) Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 1277.
18. (d) Chatterjee, A. K.; Choi, T.-L.; Grubbs, R. H. Synlett 2001, 1034.
19. (e) Choi, T.-L.; Lee, C. W.; Chatterjee, A. K.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 10417.
20. (f) Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 807.
21. (g) Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939.
22. (h) Toste, F. D.; Chatterjee, A. K.; Grubbs, R. H. Pure Appl. Chem. 2002, 74, 7.
23. (i) Chatterjee, A. K.; Toste, F. D.; Choi, T.-L.; Grubbs, R. H. Adv. Synth. Catal. 2002, 344, 634.
24. (j) Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 3171.
25. The following review on olefin metathesis comments on the lack of a general model for selectivity in CM: Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036; Angew. Chem. 1997, 109, 2124. For a recent review on cross metathesis, see: Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
26. The following review on olefin metathesis comments on the lack of a general model for selectivity in CM: Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036; Angew. Chem. 1997, 109, 2124. For a recent review on cross metathesis, see: Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
27. The following review on olefin metathesis comments on the lack of a general model for selectivity in CM: Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036; Angew. Chem. 1997, 109, 2124. For a recent review on cross metathesis, see: Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
28. Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A. ; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58.
29. Warwel, S.; Winkelmuller, W. J. Mol. Catal. 1985, 28, 247.
30. (a) Feher, F. J.; Soulivong, D.; Eklund, A. G.; Wyndham, K. D. Chem. Commun. 1997, 1186.
31. (b) Biagini, S. C. G.; Gibson, S. E.; Keen, S. P. J. Chem. Soc., Perkin Trans. 1 1998, 2485.
32. (c) Huwe, C. M.; Woltering, T. J.; Jiricek, J.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. 1999, 773.
33. (d) Seshadri, H.; Lovely, C. J. Org. Lett. 2000, 2, 327.
34. (e) Eichelberger, U.; Mansourova, M.; Henning, L.; Findeisen, M.; Giesa, S.; Muller, D.; Welzel, P. Tetrahedron 2001, 57, 9737.
35. (f) Yammamoto, Y.; Takahashi, M.; Miyaura, N. Synlett 2002, 128.
36. (a) Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998.
37. (b) Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117.
38. Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162.
39. (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
40. (b) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403.
41. Brummer, O.; Ruckert, A.; Blechert, S. Chem.-Eur. J. 1997, 3, 441.
42. Feng, J.; Schuster, M.; Blechert, S. Synlett 1997, 129.
43. (a) Pietraszuk, C.; Marciniec, B.; Fischer, H. Organometallics 2000, 19, 913.
44. (b) Kujawa-Welten, M.; Pietraszuk, C.; Marciniec, B. Organometallics 2002, 21, 840.
45. Blanco, O. M.; Castedo, L. Synlett 1999, 557.
46. Faure, S.; Piva-Le Blanc, S.; Piva, O. Tetrahedron Lett. 1999, 40, 6001.
47. Langer, P.; Holtz, E. Synlett 2001, 110.
48. Zhang, L.; Herndon, J. W. Tetrahedron Lett. 2002, 43, 4471.
49. Maishal, T. K.; Sinha-Mahapatra, D, K.; Paramjape, K.; Sarkar, A. Tetrahedron Lett. 2002, 43, 2263.
50. Grela, K.; Bieniek, M. Tetrahedron Lett. 2001, 42, 6425.
51. Imhof, S.; Randl, S.; Blechert, S. Chem. Commun. 2001, 1692.
52. BouzBouz, S.; Cossy, J. Org. Lett. 2001, 3, 1451.
53. BouzBouz, S.; De Lemos, E.; Cossy, J. Adv. Synth. Catal. 2002, 344, 627.