Effects of temperature and concentration in some ring closing metathesis reactions

Tetrahedron Letters

Volumn 44, Issue 16, 2003, Pages 3297-3299

  Yamamoto, Kana ^a   Biswas, Kaustav ^a   Gaul, Christoph ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Epothilone; Product distribution; Radicicol; RCM; Ring closing metathesis

Indexed keywords

EPOTHILONE DERIVATIVE; LACTONE DERIVATIVE; MONOMER; NATURAL PRODUCT; OLIGOMER; RADICICOL; TOLUENE;

ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); DILUTION; NUCLEAR MAGNETIC RESONANCE; OBSERVATION; RING CLOSING METATHESIS; TEMPERATURE SENSITIVITY;

EID: 0037436934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00618-X     Document Type: Article

References (33)

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14. Obtained as a mixture of more than two macrocyclic dimers.
15. The importance of the solvent effect in catalyst activity was previously reported (Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207). However, the impact on the product distribution was found insignificant in our case (see entries 2 and 3).
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18. Selected examples of reversible olefin metathesis: (a) Marsella, N. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 1101-1103; (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316; (c) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147; (d) Smith, A. B., III; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 121, 990-991; (e) Wu, Y.; Liao, X.; Wang, R.; Xie, X. S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
19. Selected examples of reversible olefin metathesis: (a) Marsella, N. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 1101-1103; (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316; (c) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147; (d) Smith, A. B., III; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 121, 990-991; (e) Wu, Y.; Liao, X.; Wang, R.; Xie, X. S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
20. Selected examples of reversible olefin metathesis: (a) Marsella, N. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 1101-1103; (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316; (c) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147; (d) Smith, A. B., III; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 121, 990-991; (e) Wu, Y.; Liao, X.; Wang, R.; Xie, X. S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
21. Selected examples of reversible olefin metathesis: (a) Marsella, N. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 1101-1103; (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316; (c) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147; (d) Smith, A. B., III; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 121, 990-991; (e) Wu, Y.; Liao, X.; Wang, R.; Xie, X. S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
22. Selected examples of reversible olefin metathesis: (a) Marsella, N. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 1997, 36, 1101-1103; (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316; (c) Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147; (d) Smith, A. B., III; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 121, 990-991; (e) Wu, Y.; Liao, X.; Wang, R.; Xie, X. S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245-3253.
23. General procedure. A stirring solution of diene in anhydrous toluene (0.2 mM) under Ar was heated to 110°C (reflux temperature) and 5-10 mol% Grubbs Ru-dihydroimidazolylidene catalyst (Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956) was added to the refluxing solution. Stirring was continued for 5-10 min, and then the flask was immersed in an ice bath. The reaction mixture was passed through a pad of silica gel, which was rinsed with methylene chloride, concentrated, and purified by flash chromatography.
24. 8b.
25. 9e.
26. Biswas K., Lin H., Njardarson J.T., Chappell M.D., Chou T.C., Guan Y., Tong W.P., He L., Horwitz S.B., Danishefsky S.J. J. Am. Chem. Soc. 124:2002;9825-9832.
27. For a detailed study of the behavior of certain ene-diene systems in ring closing metathesis, see: Paquette L.A., Basu K., Eppich J.C., Hofferberth J.E. Helv. Chim. Acta. 85:2002;3033-3051.
28. The stereoselectivity of ring closing metathesis reactions was reported to be altered by temperature: Arisawa M., Kato C., Kaneko H., Nishida A., Nakagawa M. J. Chem. Soc., Perkin Trans. 1. 2000;1873-1876.
29. For stability and decomposition studies on Grubbs catalyst, see: Ulman M., Grubbs R.H. J. Org. Chem. 64:1999;7202-7207.
30. Higher reaction temperature has been reported to favor intramolecular cyclization: Hammond, P. J.; Beer, B. D.; Hall, C. D. J. Chem. Soc., Chem. Commun. 1983, 1161-1163. Also, higher reaction temperatures favor the formation of cyclic oligomers with smaller ring size: Seebach, D.; Brändli, U.; Schnurrenberger, P.; Przybylski, M. Helv. Chim. Acta 1988, 71, 155-167. However, in some cases other factors can override the temperature effect: Picard, D.; Cazaux, L.; Tisnes, P. Tetrahedron 1986, 42, 3503-3519.
31. Higher reaction temperature has been reported to favor intramolecular cyclization: Hammond, P. J.; Beer, B. D.; Hall, C. D. J. Chem. Soc., Chem. Commun. 1983, 1161-1163. Also, higher reaction temperatures favor the formation of cyclic oligomers with smaller ring size: Seebach, D.; Brändli, U.; Schnurrenberger, P.; Przybylski, M. Helv. Chim. Acta 1988, 71, 155-167. However, in some cases other factors can override the temperature effect: Picard, D.; Cazaux, L.; Tisnes, P. Tetrahedron 1986, 42, 3503-3519.
32. Higher reaction temperature has been reported to favor intramolecular cyclization: Hammond, P. J.; Beer, B. D.; Hall, C. D. J. Chem. Soc., Chem. Commun. 1983, 1161-1163. Also, higher reaction temperatures favor the formation of cyclic oligomers with smaller ring size: Seebach, D.; Brändli, U.; Schnurrenberger, P.; Przybylski, M. Helv. Chim. Acta 1988, 71, 155-167. However, in some cases other factors can override the temperature effect: Picard, D.; Cazaux, L.; Tisnes, P. Tetrahedron 1986, 42, 3503-3519.
33. For another relevant example, see: Gaul C., Danishefsky S.J. Tetrahedron Lett. 43:2002;9039-9042.