Construction of isochromenes via a ruthenium-catalyzed reaction of oxabenzonorbornenes with propargylic alcohols

Organometallics

Volumn 26, Issue 25, 2007, Pages 6082-6090

  Villeneuve, Karine ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CYCLIZATION; CYCLOADDITION; METHANOL; OLEFINS;

ISOCHROMENES; OXABENZONORBORNENES; PROPARGYLIC ALCOHOLS;

RUTHENIUM COMPOUNDS;

EID: 37249083035     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7004518     Document Type: Article

References (74)

1. For selected examples of molecular architecture, see: (a) Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119.
2. (b) Warrener, R. N.; Margetic, D.; Sun, G.; Amarasekara, A. S.; Foley, P.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1999, 40, 4111.
3. (c) Warrener, R. N.; Butler, D. N.; Margetic, D.; Pfeffer, F. M.; Russell, R. A. Tetrahedron Lett. 2000, 41, 4671.
4. (d) Warrener, R. N.; Margetic, D.; Foley, P.; Butler, D. N.; Winling, A.; Beales, K. A.; Russell, R. A. Tetrahedron 2001, 57, 571.
5. (e) Dalphond, J.; Bazzi, H. S.; Kahrim, K.; Sleiman, H. F. Macromol. Chem. Phys. 2002, 203, 1988.
6. (f) Warrener, R. N. Eur. J. Org. Chem. 2000, 3363.
7. Lautens, M.; Fagnou, K.; Heibert, S. Acc. Chem. Res. 2003, 36, 48.
8. Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884 and references therein.
9. (a) Lautens, M.; Hiebert, S.; Renaud, J.-L. J. Am. Chem. Soc. 2001, 123, 6834.
10. (b) Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437.
11. (c) Cabrera, S.; Arrayás, R. G.; Alonso, I.: Carretero, J. C. J. Am. Chem. Soc. Chem. 2005, 127, 17938.
12. (d) Li, M.; Yan, X.-X.; Zhu, X.-Z.; Cao, B.-X.; Sun, J.; Hou, X.-L. Org. Lett. 2004, 6, 2833 and references therein.
13. Wu, M.-S.; Jeganmohan. M.; Cheng, C.-H. J. Org. Chem. 2005, 70, 9545.
14. (a) Villeneuve, K.; Jordan, R. W.; Tam, T. Synlett 2003, 2123.
15. (b) Villeneuve, K.; Tam, W. Organometallics 2006, 25, 843.
16. (c) Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514.
17. For a review on the use of Cp*Ru(COD)Cl, see: Dérien, S.; Dixneuf, P. H. J. Organomet. Chem. 2004, 689, 1382.
18. For a general review on ruthenium-catalyzed reactions, see: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
19. (b) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
20. (c) Topics in Organometallic Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer-Verlag GmbH: Berlin, New York, 2004; Vol. 11.
21. (d) Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinhein, 2004.
22. For selected examples, see: (a) Morisaki, Y.; Kondo, T.; Mitsudo, T. Organometallics 1999, 18, 4742.
23. (b) Tanaka, D.; Sato, Y.; Mori, M. Organometallics 2006, 25, 799.
24. (c) Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
25. (d) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310.
26. For some of the preliminary results of this work, see: Villeneuve, K.; Tam, W. Eur. J. Org. Chem. 2006, 5449.
27. (a) Lacassagne, A.; Buu-Hoi, N. P.; Zajdela, F.; Stora, F.; Mangane, M.; Jacquignon, P. C. R. Seances Acad. Sci., Ser. D 1971, 272, 3102.
28. (b) Thines, E.; Anke, H.; Sterner, O. J. Nat. Prod. 1998, 61, 306.
29. (c) Wang, W.; Li, T.; Milbum, R.; Yates, J.; Hinnant, E.; Luzzio, M. J.; Noble, S. A.; Attardo, G. Bioorg. Med. Chem. Lett. 1998, 8, 1579.
30. (d) Poch, G. K.; Gloer, J. B. Tetrahedron Lett. 1989, 30, 3483.
31. (e) Hari, L.; De Buyck, L. F.; Pooter, H. L. Phytochemistry 1991, 30, 1726.
32. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
33. (b) Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496.
34. (c) Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. J. Am. Chem. Soc. 2003, 124, 9028.
35. (d) Patil, N. T.; Yamamoto, Y. J. Org. Chem. 2004, 69, 5139.
36. (e) Yue, D.; Delia Cá, N.; Larock, R. C. Org. Lett. 2004, 6, 1581.
37. (f) Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. J. Org. Chem. 2005, 70, 10096.
38. (g) Yue, D.; Della Cá, N.; Larock, R. C. J. Org. Chem. 2006, 71, 3381.
39. (h) Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
40. Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A.; T.; Wills, M. J. Org. Chem. 2001, 66, 3284.
41. Le Strat, F.; Harrowven, D. C.; Maddaluno, J. J. Org. Chem. 2005, 70, 489.
42. Li, X.; Chianese, A. R.; Vogel, T.; Crabtree, R. H. Org. Lett. 2005, 7, 5437.
43. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2006, 8, 621.
44. Kusama, H.; Sawada, T.; Okita, A.; Shiozawa, F.; Iwasawa, N. Org. Lett. 2006, 8, 1077.
45. Lough, A. J.; Villeneuve, K.; Tam, W. Acta Crystallogr. 2006, E62, o2582.
46. In THF, the 5a:6a ratio for the reaction with 4a was 31:69, whereas 54:46 was obtained with 4a-d; see ref 6b.
47. Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 31, 580.
48. Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
49. Such chloride ion effects have been previously reported for CpRu-(COD)Cl, see: Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
50. Strongly complexing molecules are believed to prevent the crucial oxidative cyclization step, see: (a) Yamamoto, Y.; Nakagai, Y.; Itoh, K. Chem.-Eur. J. 2004, 10, 231.
51. (b) Reference 21.
52. (a) Trost, B. M.; Dyker, G.; Kulawiec, R. J. J. Am. Chem. Soc. 1990, 112, 7809.
53. (b) Trost, B. M.; Brown, R. E.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 5877.
54. Trost, B. M.; Probst, G. D.; Schoop, A. J. Am. Chem. Soc. 1998, 120, 9928.
55. Yamamoto, Y.; Kitahara, H.; Hattori, R.; Itoh, K. Organometallics 1998, 17, 1910.
56. Similar argument has been presented for the use of acetonitrile in other Ru-catalyzed processes, see: Kondo, T.; Morisaki, Y.; Uenoyama, S.; Wada, K.; Mitsudo, T. J. Am. Chem. Soc. 1999, 121, 8657.
57. Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
58. Burton, R. R.: Tam, W. Tetrahedron Lett. 2006, 47, 7185.
59. Ion-pairing is known to considerably affect chemical reactions, see: Macchioni, A. Chem. Rev. 2005, 105, 2039.
60. In our previous report on ruthenium-catalyzed cyclopropanation of oxabicyclic alkenes with propargylic alcohols, a 1,2-hydride migration was also postulated as another possible path. This is, however, probably not at play, because the variation of the products distribution with the solvent polarity is of small magnitude. This change is probably due to a better ionization of the chloride in more polar solvents,
61. Ruthenium carbene rearrangements have been proposed in other ruthenium-catalyzed reactions, see: (a) Reference 24a.
62. (b) Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1992, 114, 5579.
63. Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606.
64. It was hoped that product A could be isolated. A possible reason for this unreactivity towards intramolecular cyclopropanation would be the formation of a chelated subtrate-carbene complex such as B that would prevent this pathway. equation is presented Similar stable complexes have been previously described, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. F. Acc. Chem. Res. 1995, 28, 446.
65. (b) Feldman, J.; Murdzek, J. S.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 2260.
66. (a) Monnier, F.; Castillo, D.; Dérien, S.; Toupet, L.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2003, 42, 5474.
67. (b) Eckert, M.; Monnier, F.; Shchetnikov, G. T.; Titanyuk, I. D.; Osipov, S. N.; Toupet, L.; Dérien, S.; Dixneuf, P. H. Org. Lett. 2005, 7, 3741.
68. In general, ruthenium carbenes undergo metathesis or cyclopropanation reaction. For reviews on ruthenium-catalyzed metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
69. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
70. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
71. For reviews covering cyclopropanation involving ruthenium carbenes, see ref 7. For other non-metathesis reactions, see: Alcaide, B.; Almendros, P. Chem.-Eur. J. 2003, 9, 1259.
72. 2
73. (Amir-Ebrahimi, V.; Corry, D. A.; Hamilton, J. G.; Thompson, J. M.; Rooney, J. J. Macromolecules 2000, 33, 717.
74. Amir-Ebrahimi, V.; Rooney, J. J. J. Mol. Catal. A 2004, 212, 107).