Rhodium-catalyzed tandem conjugate addition-Mannich cyclization reaction: Straightforward access to fully substituted tetrahydroquinolines

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5658-5661

  So, Won Youn ^a   Song, Ju Hyun ^b   Jung, Dai Il ^b  

^a Pukyong National University   (South Korea)

^b Dong A University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; CHEMICAL REACTIONS; CYCLIZATION; HYDROCARBONS; NITROGEN COMPOUNDS; OLEFINS;

AMERICAN CHEMICAL SOCIETY (ACS); ARYL BORONIC ACIDS; CHEMICAL EQUATIONS; CONJUGATE ADDITIONS; ELECTRON DEFICIENT; ELECTROPHILE; MANNICH CYCLIZATION REACTION; RHODIUM-CATALYZED; TANDEM REACTIONS; TETRAHYDROQUINOLINES;

RHODIUM;

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; IMINE; QUINOLINE DERIVATIVE; RHODIUM;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; ELECTRON; MANNICH CYCLIZATION REACTION;

EID: 48249099656     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800914c     Document Type: Article

References (64)

1. For reviews, see: (a) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
2. (b) Negishi, E.; Copéret, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
3. (c) Tietze, L. F. Chem. Rev. 1996, 96, 115.
4. (d) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
5. (e) Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
6. For recent examples, see: (f) Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528.
7. (g) Subburaj, K.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 11210.
8. (h) Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354.
9. For examples of Rh(I)-catalyzed tandem cyclization reactions, see: (a) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
10. (b) Bocknack, B. M.; Wang, L.-C.; Krische, M. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5421.
11. (c) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54.
12. (d) Miura, T.; Murakami, M. Org. Lett. 2005, 7, 3339.
13. (e) Miura, T.; Harumashi, T.; Murakami, M. Org. Lett. 2007, 9, 741.
14. (f) Miura, T.; Takahashi, Y.; Murakami, M. Org. Lett. 2007, 9, 5075.
15. (g) Miura, T.; Shimada, M.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1094.
16. (h) Lautens, M.; Mancuso, J. Org. Lett. 2002, 4, 2105.
17. (i) Lautens, M.; Mancuso, J. J. Org. Chem. 2004, 69, 3478.
18. (j) Lautens, M.; Marquardt, T. J. Org. Chem. 2004, 69, 4607.
19. (k) Shintani, R.; Tsurusaki, A.; Okamoto, K.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 3909.
20. (l) Chen, Y.; Lee, C. J. Am. Chem. Soc. 2006, 128, 15598.
21. (m) Navarro, C.; Csákÿ, A. G., Org. Lett. 2008, 10, 217.
22. For examples of Rh(I)-catalyzed tandem noncyclization reactions, see: (a) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
23. (b) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Organomet. Chem. 2002, 648, 297.
24. (c) Kurahash, T.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 6336.
25. Examples of similar reactions using other transition metals. Nickel catalysis: (a) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
26. (b) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
27. (c) Jayanth, T. T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2007, 46, 5921.
28. Ir catalysis: (d) Nishimura, T.; Yasuhara, Y.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 7506.
29. Pd catalysis: (e) Nishikata, T.; Kobayashi, Y.; Kobayashi, K.; Yamamoto, Y.; Miyaura, N. Synlett 2007, 3055.
30. (f) Tsukamoto, H.; Kondo, Y. Org. Lett. 2007, 9, 4227.
31. (g) Tsukamoto, H.; Ueno, T.; Kondo, Y. Org. Lett. 2007, 9, 3033.
32. (h) Tsukamoto, H.; Matsumoto, T.; Kondo, Y. J. Am. Chem. Soc. 2008, 130, 388, and references therein.
33. Tandem reactions using imine as a secondary electrophile. Nickel catalysis: ref 4a,b. Pd catalysis: ref 4g.
34. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
35. (b) Hayashi, T. Synlett 2001, 879.
36. (c) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
37. (d) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
38. (e) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13.
39. For selected examples, see: (a) Wang, Z.-Q.; Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. J. Am. Chem. Soc. 2007, 129, 5336.
40. (b) Marelli, C.; Monti, C.; Gennari, C.; Piarulli, U. Synlett 2007, 2213.
41. (c) Duan, H.-F.; Jia, Y.-X.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2006, 8, 2567.
42. (d) Kuriyama, M.; Soeta, T.; Hao, X.; Chen, Q.; Tomioka, K. J. Am. Chem. Soc. 2004, 126, 8128.
43. (e) Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31.
44. (a) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
45. (b) Steinhagen, H.; Corey, E. J. Org. Lett. 1999, 1, 823.
46. (c) Dannhardt, G.; Gruchalla, M. V.; Kohl, B. K.; Parsons, C. G. Arch. Pharm. 2000, 333, 267.
47. (d) Hoemann, M. Z.; Xie, R. L.; Ross, R. F.; Meyer, S.; Sidhu, A.; Cunny, G. D.; Hauske, J. R. Bioorg. Med. Chem. Lett. 2002, 12, 129.
48. (e) Smith, H. C.; Cavanaugh, C. K.; Friz, J. L.; Thompson, C. S.; Saggers, J. A.; Michelotti, E. L.; Garcia, J.; Tice, C. M. Bioorg. Med. Chem. Lett. 2003, 13, 1943.
49. (f) Theeraladanon, C.; Arisawa, M.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2005, 16, 827.
50. (g) Liu, H. M.; Liu, F. W.; Zou, D. P.; Dai, G. F. Bioorg. Med. Chem. Lett. 2005, 15, 1821.
51. There is one example for Rh(I)-catalyzed synthesis of 3-alkylideneoxindoles using isocyanates as a secondary electrophile; see ref 2f.
52. (a) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
53. (b) Pastine, S. J.; Youn, S. W.; Sames, D. Tetrahedron 2003, 59, 8859.
54. (c) Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
55. (d) Youn, S. W.; Eom, J. I. Org. Lett. 2005, 7, 3355.
56. (e) Youn, S. W. J. Org. Chem. 2006, 71, 2521.
57. (f) Youn, S. W. Org. Prep. Proced. Int. 2006, 38, 505.
58. (g) Youn, S. W.; Eom, J. I. J. Org. Chem. 2006, 71, 6705.
59. (h) Youn, S. W. Synlett 2007, 3050.
60. 3 were detrimental to the reaction presented herein (see Supporting Information). It has been reported that boric acid is presumed to facilitate the release of rhodium from the iminorhodium(I) intermediate by protonolysis in the Rh-catalyzed reaction of ethyl cyanoformate with arylboronic acids; see: Shimizu, H.; Murakami, M. Chem. Commun. 2007, 2855.
61. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
62. (a) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805.
63. (b) Miura, T.; Shimada, M.; Ku, S.-Y.; Tamai, T.; Murakami, M. Angew. Chem., Int. Ed. 2007, 46, 7101.
64. (c) Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876.