Epimerization reaction of a substituted vinylcyclopropane catalyzed by ruthenium carbenes: Mechanistic analysis

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8864-8875

  Zeng, Xingzhong ^a   Wei, Xudong ^a   Farina, Vittorio ^a   Napolitano, Elio ^b   Xu, Yibo ^a   Zhang, Li ^a   Haddad, Nizar ^a   Yee, Nathan K ^a   Grinberg, Nelu ^a   Shen, Sherry ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; RATE CONSTANTS; RUTHENIUM COMPOUNDS; SUBSTITUTION REACTIONS;

EPIMERS; EQUILIBRIUM RATIO; GRUBBS CATALYST; VINYLCYCLOPROPANES;

OLEFINS;

CARBENOID; CYCLOPROPANE DERIVATIVE; LIGAND; NITROGEN; PHOSPHINE; RUTHENACYCLOPENTENE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLCYCLOPROPANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; EPIMER; EPIMERIZATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLOPROPANES; HYDROCARBONS; METHANE; MODELS, CHEMICAL; MOLECULAR CONFORMATION; RUTHENIUM; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 33750883224     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061587o     Document Type: Article

References (69)

1. For recent reviews on olefin metathesis, see: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
2. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
3. (c) Grubbs, R. H., Ed. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003.
4. For a recent highlight review, see: Alcaide, B.; Almendros, P. Chem.-Eur. J. 2003, 9, 1259.
5. Tallarico, J. A.; Malnick, L. A.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
6. (a) Joe, D.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8635.
7. (b) Fürstner, A.; Theil, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
8. (a) Hu, Y.-J.; Dominique, R.; Das, S. K.; Roy, R. Can. J. Chem. 2000, 78, 838.
9. (b) Cadot, C.; Dalko, P. I.; Cossy, J. Tetrahedron Lett. 2002, 43, 1839.
10. (c) Hoye, T. R.; Zhao, H. Org. Lett. 1999, 1, 1123.
11. (d) Nakashima, K.; Ito, R.; Sono, M.; Tori, M. Heterocycles 2000, 53, 301.
12. (e) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781.
13. (f) Application in total synthesis of (-)-tuberostemonine: Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848-14849.
14. (g) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390-13391.
15. (h) Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2002, 41, 4732.
16. (i) Braddock, D. C.; Matsuno, A. Tetrahedron Lett. 2002, 43, 3305.
17. (j) Braddock, D. C.; Wildsmith, A. J. Tetrahedron Lett. 2001, 42, 3239.
18. (a) Bielawski, C. W.; Louie, J.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 12872.
19. (b) Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196.
20. Schmidt, B. Eur. J. Org. Chem. 2004, 1865.
21. Tsantrizos, Y. S.; Bolger, G.; Bonneau, P.; Cameron, D. R.; Goudreau, N.; Kukolj, G.; LaPlante, S. R.; Llinàs-Brunet, M.; Nar, H.; Lamarre, D. Angew. Chem., Int. Ed. 2003, 42, 1356.
22. Poirier, M.; Asubry, N.; Boucher, C.; Ferland, J.-M.; LaPlante, S.; Tsantrizos, Y. S. J. Org. Chem. 2005, 70, 10765.
23. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
24. Beaulieu, P. L.; Gillard, J.; Bailey, M. D.; Boucher, C.; Duceppe, J.-S.; Simoneau, B.; Wang, X.-J.; Zhang, L.; Grozinger, K.; Houpis, I.; Farina, V.; Heimroth, H.; Krueger, T.; Schnaubelt, J. J. Org. Chem. 2005, 70, 5869.
25. 22D: found +61°, lit. +64°. See: Alcarza, C.; Herrero, A.; Marco, J. L.; Fernandez-Alvarez, E.; Bernabe, M. Tetrahedron Lett. 1992, 33, 5605.
26. Yee, N. K.; Farina, V.; Houpis, I. N.; Haddad, N.; Frutos, R. P.; Gallou, F.; Wang, X.-J.; Wei, X.; Simpson, R. D.; Feng, X.; Fuchs, V.; Xu, Y.; Tan, J.; Zhang, L.; Xu, J.; Smith-Keenan, L. L.; Vitous, J.; Ridges, M. D.; Spinelli, E. M.; Johnson, M.; Donsbach, K.; Nicola, T.; Brenner, M.; Winter, E.; Kreye, P.; Samstag, W. J. Org. Chem. 2006, 71, 7133.
27. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543.
28. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
29. 31P NMR spectrum consists of a singlet, even though the two P centers are diastereotopic. However, the cooling of a solution of 18 and 19 in CD2Ch to -90 °C evidenced the expected four doublets. The dynamic NMR behavior of these and related complexes will be the subject of a forthcoming study.
30. Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484.
31. Adlhart, C.; Hinderung, C.; Baumann, H.; Chen, P. J. Am. Chem. Soc. 2000, 122, 8204.
32. Gurjar, M. K.; Yakambram, P. Tetrahedron Lett. 2001, 42, 3633.
33. Frisch, M. J.; et al. Gaussian 98, Revision A.6; Gaussian Inc.: Pittsburgh, PA, 1998.
34. For a practical guide, see: Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods; Gaussian Inc.: Pittsburgh, PA, 1996.
35. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785.
37. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
38. Dunning, T. H.; Hay, P. G. In Modem Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
39. Niu, S.; Hall, M. B. Chem. Rev. 2000, 100, 353.
40. Dedieu, A. Chem. Rev. 2000, 100, 543.
41. (a) Yang, Z.-Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881.
42. (b) Yamamoto, K.; Biswas, K.; Gaul, C.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 3297.
43. (c) Barrett, A. G. M.; Hamprecht, D.; James, R. A.; Ohkubo, M.; Procopiou, P. A.; Toledo, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2001, 66, 2187.
44. (d) Verbicky, C. A.; Zercher, C. K. Tetrahedron Lett. 2000, 41, 8723.
45. Bourgeois, D.; Pancrazi, A.; Nolan, S. P.; Prunet, J. J. Organomet. Chem. 2002, 643-644, 247.
46. McGrath, D. V.; Grubbs, R. H. Organometallics 1994, 13, 224.
47. Hong, S. H.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 7414.
48. Dinger, M.; Mol, J. C. Organometallics 2003, 22, 1089.
49. Schmidt, B. Chem. Commun. 2004, 742.
50. (a) Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277.
51. (b) Fürstner, A.; Thiel, O. R.; Lehmann, C. W. Organometallics 2002, 21, 331.
52. (c) McNaughton, B. R.; Bucholtz, K. M.; Camaaño-Moure, A.; Miller, B. L. Org. Lett. 2005, 7, 733.
53. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
54. This possibility was first proposed by Tsantrizos et al.; see ref 10.
55. 3 by adventitious oxygen.
56. Trost, B. M.; Pinkerton, A. B.; Toste, F. D.; Sperrle, M. J. Am. Chem. Soc. 2001, 123, 12504.
57. Itami, K.; Mitsudo, K.; Fujita, K.; Ohashi, Y.; Yoshida, J.-I. J. Am. Chem. Soc. 2004, 126, 11058.
58. Jordan, R. W.; Khoury, P. R.; Goddard, J. D.; Tam, W. J. Org. Chem. 2004, 69, 8467.
59. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
60. (a) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
61. (b) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
62. (c) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
63. Secondary aliphatic amines are rare as the Ru ligand in metathetical processes, but mixed piperidino/phosphino-Ru-carbene complexes have been implicated in the ROMP of norbornene: (a) Matos, J. M. E.; Lima-Neto, B. S. J. Mol. Catal. A: Chem. 2004, 222, 82.
64. Pyridine-Ru-carbene complexes are well-known as rapid initiators: (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314.
65. (c) Love, J. A.; Sanford, M. S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 10103.
66. (d) Bai, C.-X.; Zhang, W.-Z.; He, R.; Lu, X.-B.; Zhang, Z.-Q. Tetrahedron Lett. 2005, 46, 7225.
67. For a novel relay strategy, see: (a) Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210.
68. See also: (b) Wallace, D. J. Angew. Chem., Int. Ed. 2005, 44, 1912 and references therein.
69. Eckert, M.; Monnier, F.; Shchetnikov, G. T.; Titanuyk, I. D.; Osipov, S. N.; Toupet, L.; Dérien, S.; Dixneuf, P. H. Org. Lett. 2005, 7, 3741.