Asymmetric Synthesis of Functionalized 1,2,3,4-Tetrahydroquinolines

Organic Letters

Volumn 3, Issue 13, 2001, Pages 2053-2056

  Gallou Dagommer, Isabelle ^a   Gastaud, Philippe ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDRO 2 METHYLQUINOLINE; 2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; ANTIOXIDANT; PESTICIDE; PHOTOSENSITIZING AGENT; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ANTIOXIDANTS; PESTICIDES; PHOTOSENSITIZING AGENTS; QUINOLINES;

EID: 0035963684     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016018b     Document Type: Article

References (56)

1. Michael, J. P. Nat. Prod. Rep. 1997, 14, 605-618.
2. (b) Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; McKillop, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 5, Chapter 5.06, pp 245-300.
3. (c) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785. For two recent reports, see:
4. (d) De Kempe, N.; Keppens, M. Tetrahedron 1996, 52, 3705-3718.
5. (e) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595-3607.
6. (a) Katritsky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031-15070.
7. (b) Leeson, P. D.; Carling, R. W.; Moore, K. W.; Mosely, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954-1968.
8. (c) Nagata, R.; Tanno, N.; Kodo, T.; Ae, N.; Yamaguchi, H.; Tamiki, N.; Antoku, F.; Tatsuno, T.; Kato, T.; Tanaka, Y.; Nakamura, M. J. J. Med. Chem. 1994, 37, 3956-3968.
9. For an extensive listing, see ref 2a.
10. (a) Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, H. G. J. Org. Chem. 1986, 51, 5478-5480.
11. (b) Konishi, M.; Ohkuma, H.; Tsuno, T.; Oki, T.; VanDuyne, G. D.; Clardy, I. J. Am. Chem. Soc. 1990, 112, 3715-3716.
12. (c) Omura, S.; Nakagawa, A. Tetrahedron Lett. 1981, 22, 2199-2202.
13. (a) Ohba, K.; Watabe, H.; Sasaki, T.; Takeuchi, Y.; Kodama, Y.; Nakazawa, T.; Yamamoto, H.; Shomura, T.; Sezaki, M.; Kondo, S. J. Antibiot. 1988, 41, 1515-1519.
14. (b) Ishii, S.; Nagasawa, M.; Kariya, Y.; Yamamoto, H.; Inouye, S.; Kondo, S. J. Antibiot. 1989, 42, 1713-1717.
15. (c) Ogawa, T.; Ichimura, M.; Katsumata, S.; Morimoto, M. Takahashi, K. J. Antibiot. 1989, 42, 1299-1301.
16. (d) Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1988, 43, 378-391.
17. (d) Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Goldberg, J. A. Chem. Rev. 1997, 97, 787-828, and references therein.
18. (a) Muratake, H.; Abe, I.; Natsume, M. Chem. Pharm. Bull. 1996, 44, 67-79.
19. (b) Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573-2576. This spirocyclization was initially proposed by Boger et al. in connection with biochemical studies of Duocarmycins, Boger, D. L.; Ishizaki, T.; Zarrinmayeh, M.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1990, 112, 8961-8971. Boger's synthesis of Duocarmycin A also used the trans-annular cyclization. See ref 7.
20. (b) Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573-2576. This spirocyclization was initially proposed by Boger et al. in connection with biochemical studies of Duocarmycins, Boger, D. L.; Ishizaki, T.; Zarrinmayeh, M.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. J. Am. Chem. Soc. 1990, 112, 8961-8971. Boger's synthesis of Duocarmycin A also used the trans-annular cyclization. See ref 7.
21. Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. Goldberg, J. A. J. Am. Chem. Soc. 1997, 119, 311-325. The low enantioselectivity (78% ee) of the reaction necessitated preparative HPLC purification of the intermediates before further steps in the synthesis of Duocarmycin A. For the synthesis of related molecules using asymmetric epoxidation see: Boger, D. L.; McKie, J. A.; Boyce, C. W. Synlett 1997, 515-517.
22. Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. Goldberg, J. A. J. Am. Chem. Soc. 1997, 119, 311-325. The low enantioselectivity (78% ee) of the reaction necessitated preparative HPLC purification of the intermediates before further steps in the synthesis of Duocarmycin A. For the synthesis of related molecules using asymmetric epoxidation see: Boger, D. L.; McKie, J. A.; Boyce, C. W. Synlett 1997, 515-517.
23. For other reports of the use of asymmetric catalysis in the construction of tetrahydroquinolines see: (a) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357-7360.
24. (b) Katayama, S.; Nagata, T. Japan Patent JP 08333345 A2, 1996; Chem. Abstr. 1997, 126, 157407.
25. (b) Katayama, S.; Nagata, T. Japan Patent JP 08333345 A2, 1996; Chem. Abstr. 1997, 126, 157407.
26. (c) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327-6328.
27. (d) Morimoto, Y.; Oda, K.; Shirahama, H.; Matsumoto, T.; Omura, S. Chem. Lett. 1988, 909-912.
28. For recent reviews see: (a) Brown, J. M. Chem. Soc. Rev. 1993, 25-41.
29. (b) Brown, J. M. Hydrogenation of Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp 121-182.
30. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. Asymmetric Hydrogenation. In Catalytic Asymmetric Syntheis; Ojima, I., Ed.; John Wiley: New York, 2000; pp 1-110.
31. (a) RajanBabu, T. V.; Ayers, T. A.; Casalnuovo, A. L. J. Am. Chem. Soc. 1994, 116, 4101-4102.
32. (b) RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012-6028.
33. See Supporting Information for details of experimental procedures, characterization of intermediates, and chromatographic determinations of enantiomeric excesses. The nitro compound 10a can be reduced quantitatively (5% Pd/C, 15 mol %, THF/MeOH) to the amino compound 10b, potentially useful for the synthesis of 3-aminoquinolones.
34. (a) Cutolo, M.; Fiandanese, V.; Naso, F.; Sciacovelli, O. Tetrahedron Lett. 1983, 24, 4603.
35. (b) Harrington, P. H.; Hegedus, L. S. J. Org. Chem. 1984, 49, 2657-2662.
36. (c) Bozell, J. J.; Vogt, C. E.; Gozum, J. J. Org. Chem. 1991, 56, 2584-2587.
37. 11
38. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
39. 11
40. Mesylation leads to a mixture of the mono- and di-N-mesyl compounds. Also see ref 26.
41. 11
42. Plevyak, J. E.; Dickerson, J. E.; Heck, R. F. J. Org. Chem. 1979, 44, 4078-4080.
43. Examples of Sharpless epoxidation of o-substituted cinnamyl alcohol derivatives are rare; no examples of the especially valuable 2-nitrocinnamyl alcohols have been reported previously. Yields and selectivities for these reactions are generally low. See for example: (a) Medina, E.; Vidal-Ferran, A.; Moyano, A.; Pericás, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 1581-1586.
44. (b) Takahashi, K.; Ogata, M. J. Org. Chem. 1987, 52, 1877-1880.
45. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
46. Goument, B.; Duhamel, L.; Mauge, R. Tetrahedron 1994, 50, 171-188.
47. Wierenga, W. J. Am. Chem. Soc. 1981, 103, 5621-5623. See also:
48. (b) Fukuda, Y.; Itoh, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2793-2807.
49. (c) This and the subsequent experiments were conducted in the racemic series.
50. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719-2722.
51. Dai, L.; Lou, B.; Zhang, Y.; Guo, G. Tetrahedron Lett. 1986, 27, 4343-4346.
52. Bonini, C.; Righi, G.; Sotgiu, G. J. Org. Chem. 1991, 56, 6206-6209.
53. (a) Rewcastle, G. W.; Baguley, B. C.; Cain, B. F. J. Med. Chem. 1982, 25, 1231-1235.
54. (b) Verboom, W.; Orlemans, E. O. M.; Berga, H. J.; Scheltinga, M. W.; Reinhoudt, D. N. Tetrahedron 1986, 42, 5053-5064.
55. (c) Le Corre, M..; Hercouet, A.; Le Stanc, Y.; Le Baron, H. Tetrahedron 1985, 41, 5313-5320.
56. Coutts, I. G. C.; Culbert, N. J.; Edwards, M.; Hadfield, J. A.; Musto, D. R.; Pavlidis, V. H.; Richards, D. J. J. Chem. Soc., Perkin Trans. 1 1985, 1829-1836.