Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene-ynamide

Tetrahedron

Volumn 62, Issue 16, 2006, Pages 3872-3881

  Mori, Miwako ^a   Wakamatsu, Hideaki ^b   Saito, Nozomi ^c   Sato, Yukako ^c   Narita, Rie ^b   Sato, Yoshihiro ^c   Fujita, Reiko ^b  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Dienamide; Ene ynamide; Enyne metathesis; Ethylene; Indole; Quinoline

Indexed keywords

AMIDE; CARBENOID; CYCLIC DIENAMIDE; DIHYDROPYRROLIDINE DERIVATIVE; ENAMINE; INDOLE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; YNAMIDE;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; PRIORITY JOURNAL; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 33645327171     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.083     Document Type: Article

References (76)

1. For recent reviews on metathesis, see; (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
2. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
3. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833.
4. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036.
5. (e) Fürstner, A., Ed.; Topics in Organometallic Chemistry; Springer: Berlin, Heidelberg, 1998; Vol. 1.
6. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
7. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
8. (h) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75.
9. (i) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
10. (j) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
11. (k) Schrock, R. R. Tetrahedron 1999, 55, 8141.
12. (l) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945.
13. (m) Vernall, A. J.; Abell, A. D. Aldrichim. Acta 2003, 36, 93.
14. (n) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
15. (o) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
16. (p) Katz, T. J. Angew. Chem., Int. Ed. 2005, 44, 3010.
17. (q) Fürstner, A.; Davies, P. W. Chem. Commun. 2005, 2307.
18. (r) Mori, M. J. Synth. Org. Chem. Jpn. 2005, 63, 423.
19. (s) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490.
20. For reviews on enyne metathesis, see; (a) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
21. (b) Mori, M. J. Synth. Org. Chem. Jpn. 1998, 56, 115.
22. (c) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
23. (d) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
24. (e) Mori, M. J. Mol. Catal. A: Chem. 2004, 213, 73.
25. For recent applications, see; (f) Clark, J. S.; Hamelin, O. Angew. Chem., Int. Ed. 2000, 39, 372.
26. (g) Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236.
27. (h) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274.
28. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231.
29. (j) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582.
30. (k) Royer, F.; Vilain, C.; Elkaïm, L.; Grimaud, L. Org. Lett. 2003, 5, 2007.
31. (l) Lee, H.-Y.; Kim, H. Y.; Tae, H.; Kim, B. G.; Lee, J. Org. Lett. 2003, 5, 3439.
32. (m) Kaliappan, K. P.; Nandurdikar, R. S. Chem. Commun. 2004, 2506.
33. (n) Funel, J.-A.; Prunet, J. J. Org. Chem. 2004, 69, 4555.
34. (o) Kummer, D. A.; Brenneman, J. B.; Martin, S. F. Org. Lett. 2005, 7, 4621.
35. (a) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
36. (b) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356.
37. (c) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287.
38. (d) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
39. (e) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
40. (f) Kinoshita, A.; Sakakibara, N.; Mori, M. Tetrahedron 1999, 55, 8155.
41. (g) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato, Y. Org. Lett. 2000, 2, 543.
42. (h) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161.
43. (i) Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 654.
44. (j) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258.
45. (k) Mori, M.; Kuzuba, Y.; Kitamura, T.; Sato, Y. Org. Lett. 2002, 4, 3855.
46. (l) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.
47. (m) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224.
48. (n) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
49. (o) Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235.
50. (p) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397.
51. (q) Kitamura, T.; Kuzuba, Y.; Sato, Y.; Wakamatsu, H.; Fujita, R.; Mori, M. Tetrahedron 2004, 60, 7375.
52. (r) Kitamura, T.; Sato, Y.; Mori, M. Tetrahedron 2004, 60, 9649.
53. (s) Mori, M.; Wakamatsu, H.; Tonogaki, K.; Fujita, R.; Kitamura, T.; Sato, Y. J. Org. Chem. 2005, 70, 1066.
54. For recent review on the chemistry of ynamines and ynamides, see; (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575 and references cited therein.
55. For recent examples of nitrogen-heterocycles synthesis by cyclization of ynamide using transition metals, see; (b) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489.
56. (c) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426.
57. (d) Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879.
58. (e) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037.
59. (f) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
60. (g) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965.
61. (h) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
62. (i) Witulski, B.; Lumtscher, J.; Bergsträßer, U. Synlett 2003, 708.
63. (j) Couty, S.; Loégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
64. (k) Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J. Org. Lett. 2005, 7, 1047.
65. (l) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
66. For reviews on Diels-Alder reaction of dienamide, see; (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753 and references cited therein.
67. (b) Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421 and references cited therein.
68. For recent examples of preparation and reaction of dienamides, see; (c) Hübner, S.; Neumann, H.; Wangelin, A. J.; Klaus, S.; Strübing, D.; Klein, H. Synthesis 2005, 2084.
69. (d) Gauvry, N.; Huet, F. J. Org. Chem. 2001, 66, 583 and references cited therein.
70. Brückner, D. Synlett 2000, 1402.
71. Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783.
72. Compounds (Z)-9 and (E)-9 were synthesized according to literature procedure; Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans. 1 2001, 1182.
73. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
74. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
75. For precedence of solvent effect on the reactivity of the second-generation Ru-carbene complex, see; Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
76. When ene-ynamide was used as the substrate, the enyne metathesis of terminal alkyne proceeded smoothly under argon for the first time (cf. Ref. 3e). Recently, RCM of electron-rich terminal alkynes using 1 without ethylene gas has been reported (Ref. 2e,h). We continued to examine the reaction under ethylene gas, since the yield of the cyclized product that was obtained from the reaction under ethylene gas is higher than that of the cyclized product obtained from the reaction under argon.