Electrophilic bromination of N-acylated cyclohex-3-en-1-amimes: Synthesis of 7-azanorbornanes

Helvetica Chimica Acta

Volumn 87, Issue 11, 2004, Pages 2764-2789

  Kapferer, Peter ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ENZYME INHIBITION; OLEFINS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

BROMO-AMINATION; DIHYDROXYLATION; GLYCOSIDASE INHIBITORS;

BROMINE;

2 [(BENZYLOXY)METHYL] 7 [(TERT BUTOXY)CARBONYL] 5 BROMO 7 AZABICYCLO[2.2.1]HEPTANE; 2 [BENZYL[(TERT BUTOXY)CARBONYL]AMINO] 4 BROMO 6 OXABICYCLO[3.2.1]OCTANE; 2 BROMO 7 [(TERT BUTOXY)CARBONYL] 7 AZABICYCLO[2.2.1]HEPTANE; 4 BENZYL 6 [(BENZYLOXY)METHYL] 8 BROMO 2 OXA 4 AZABICYCLO[3.3.1]NONAN 3 ONE; 6 [(BENZYLOXY)METHYL] 8 BROMO 3 (TRIFLUOROMETHYL) 2 OXA 4 AZABICYCLO[3.3.1]NON 3 ENE; ACETAMIDE DERIVATIVE; ALKENE DERIVATIVE; AMINE; BORNANE DERIVATIVE; BROMINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CYCLOHEXENE DERIVATIVE; ETHER DERIVATIVE; GLYCOSIDASE INHIBITOR; KETONE DERIVATIVE; METHYL 4,5 DIBROMO 2 [[(TERT BUTOXY)CARBONYL]AMINO]CYCLOHEXANE 1 CARBOXYLATE; METHYL 5 BROMO 7 [(TERT BUTOXY)CARBONYL] 7 AZABICYCLO[2.2.1]HEPTANE 2 CARBOXYLATE; METHYL 6 [[(TERT BUTOXY)CARBONYL]AMINO]CYCLOHEX 3 ENECARBOXYLATE; METHYL 8 BROMO 3 OXO 2 OXA 4 AZABICYCLO[3.3.1]NONANE 6 CARBOXYLATE; N (3,4 DIBROMOCYCLOHEX 1 YL) 2,2,2 TRIFLUOROACETAMIDE; N (CYCLOHEX 3 ENYL) 2,2,2 TRIFLUOROACETAMIDE; N [2 [(BENZYLOXY)METHYL] 4,5 DIBROMOCYCLOHEX 1 YL] 2,2,2 TRIFLUOROACETAMIDE; N [6 [(BENZYLOXY)METHYL]CYCLOHEX 3 ENYL] 2,2,2 TRIFLUOROACETAMIDE; N BROMOSUCCINIMIDE; OXAZINE DERIVATIVE; TERT BUTYL N (CYCLOHEX 3 ENYL)CARBAMATE; TERT BUTYL N [2 [(BENZYLOXY)METHYL] 4,5 DIBROMOCYCLOHEX 1 YL]CARBAMATE; TERT BUTYL N [6 [(BENZYLOXY)METHYL]CYCLOHEX 3 ENYL]CARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; AMIDATION; ARTICLE; BROMINATION; CARBAMOYLATION; CYCLIZATION; DEPROTECTION REACTION; DIHYDROXYLATION; MOLECULAR BIOLOGY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 11144293484     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490249     Document Type: Article

References (87)

1. P. Deslongchamps, 'Stereoelectronic Effects in Organic Chemistry', Pergamon Press, Oxford, 1983.
2. C. W. Andrews, B. Fraser-Reid, J. P. Bowen, in 'The Anomeric Effect and Associated Stereoelectronic Effects', Ed. G. R. J. Thatcher, American Chemical Society, Washington, DC, 1993, 539, p. 114.
3. M. Böhm, E. Lorthiois, M. Meyyappan, A. Vasella, Helv. Chim. Acta 2003, 86, 3787.
4. A. Varrot, J. Macdonald, R. V. Stick, G. Pell, H. J. Gilbert, G. J. Davies, Chem. Commun. 2003, 946.
5. N. Asano, K. Oseki, E. Tomioka, H. Kizu, K. Matsui, Carbohydr. Res. 1994, 259, 243.
6. M. Böhm, E. Lorthiois, M. Meyyappan, A. Vasella, Helv. Chim. Acta 2003, 86, 3818.
7. S. Fort, P. M. Coutinho, M. Schülein, R. Nardin, S. Cottaz, H. Driguez, Tetrahedron Lett. 2001, 42, 3443.
8. L. Hosie, M. L. Sinnott, Biochem. J. 1985, 226, 437.
9. K. S. E. Tanaka, A. J. Bennet, Can. J. Chem. 1998, 76, 431.
10. J. W. Daly, T. Tokuyama, T. Fujiwara, R. J. Highet, I. L. Karle, J. Am. Chem. Soc. 1980, 102, 830.
11. E. J. Corey, T.-P. Loh, S. AchyuthaRao, D. C. Daley, S. Sarshar, J. Org. Chem. 1993, 58, 5600.
12. S. Robin, G. Rousseau, Tetrahedron 1998, 54, 13681.
13. E. W. Della, P. R. Jefferies, Aust. J. Chem. 1961, 14, 610.
14. J. von Braun, W. Haensel, F. Zobel, Liebigs Ann. Chem. 1928, 462, 283.
15. R. F. Parcell, J. P. Sanchez, J. Org. Chem. 1981, 46, 5228.
16. J. Tadanier, J. R. Martin, A. M. Nadzan, P. Johnson, J. Holms, R. Hallas, R. Stanaszek, M. Cirovic, D. Grampovnik, A. W. Goldstein, Carbohydr. Res. 1981, 96, 185.
17. B. A. Marples, R. C. Toon, Tetrahedron Lett. 1999, 40, 4873.
18. Z. Chen, M. L. Trudell, Chem. Rev. 1996, 96, 1179.
19. D. Bai, R. Xu, X. Zhu, Drugs Future 1997 22, 1210.
20. H. F. Olivio, M. S. Hemenway, Org. Prep. Proc. Int. 2002, 34, 1.
21. I. Gillaizeau-Gauthier, J. Royer, H.-P. Husson, Eur. J. Org. Chem. 2002, 1484.
22. R. N. Warrener, G. Sun, Tetrahedron Lett. 2001, 42, 465.
23. J.-P. G. Seerden, M. T. M. Tulp, H. W. Scheeren, C. G. Kruse, Bioorg. Med. Chem. 1998, 6, 2103.
24. A. Otten, J. C. Namyslo, M. Stoermer, D. E. Kaufmann, Eur. J. Org. Chem. 1998, 1997.
25. A. J. Moreno-Vargas, C. Schütz, R. Scopelliti, P. Vogel, J. Org. Chem. 2003, 68, 5632.
26. S. C. Clayton, A. C. Regan, Tetrahedron Lett. 1993, 34, 7493.
27. C. Zhang, M. L. Trudell, J. Org. Chem. 1996, 61, 7189.
28. S. Singh, G. P. Basmadjian, Tetrahedron Lett. 1997, 38, 6829.
29. L. E. Brieaddy, F. Liang, P. Abraham, J. R. Lee, F. I. Carroll, Tetrahedron Lett. 1998, 39, 5321.
30. G. M. P. Giblin, C. D. Jones, N. S. Simpkins, J. Chem. Soc., Perkin Trans. 1 1998, 3689.
31. C. D. Jones, N. S. Simpkins, G. M. P. Giblin, Tetrahedron Lett. 1998, 39, 1023.
32. C. Zhang, C. J. Ballay II, M. L. Trudell, J. Chem. Soc., Perkin Trans. 1 1999, 675.
33. H. F. Olivio, M. S. Hemenway, M. H. Gezginci, Tetrahedron Lett. 1998, 39, 1309.
34. R. R. Fraser, R. B. Swingle, Can. J. Chem. 1970, 48, 2065.
35. A. Avenoza, C. Cativiela, J. H. Busto, J. M. Peregrina, Tetrahedron Lett. 1995, 36, 7123.
36. C. Szantay, Z. Kardos-Balogh, I. Moldvai, J. Szantay, C., E. Temesvari-Major, G. Blasko, Tetrahedron 1996, 52, 11053.
37. H. Kosugi, M. Abe, R. Hatsuda, H. Uda, M. Kato, Chem. Commun. 1997, 1857.
38. N. S. Sirisoma, C. R. Johnson, Tetrahedron Lett. 1998, 39, 2959.
39. J. Habermann, S. V. Ley, J. S. Scott, J. Chem. Soc., Perkin Trans. 1 1999, 1253.
40. D. A. Evans, K. A. Scheidt, C. W. Downey, Org. Lett. 2001, 3, 3009.
41. S. Aoyagi, R. Tanaka, M. Naruse, C. Kibayashi, J. Org. Chem. 1998, 63, 8397.
42. J. E. Bäckvall, Pure Appl. Chem. 1999, 71, 1065.
43. B. M. Trost, G. R. Cook, Tetrahedron Lett. 1996, 37, 7485.
44. H. Nakashima, K. Hiroya, T. Taniguchi, K. Ogasawara, Synlett 1999, 1405.
45. E. Albertini, A. Barco, S. Benetti, C. De Risi, G. P. Pollini, V. Zanirato, Tetrahedron 1997, 53, 17177.
46. M. T. Barros, C. D. Maycock, M. R. Ventura, J. Chem. Soc., Perkin Trans. 1 2001, 166.
47. S. R. Fletcher, R. Baker, M. S. Chambers, R. H. Herbert, S. C. Hobbs, S. R. Thomas, H. M. Verrier, A. P. Watt, R. G. Ball, J. Org. Chem. 1994, 59, 1771.
48. J. R. Pfister, W. E. Wymann, R. M. Weissberg, A. M. Strosberg, J. Pharm. Sci. 1985, 74, 208.
49. K. C. V. Ramanaiah, N. Zhu, C. Klein-Stevens, M. L. Trudell. Org. Lett. 1999, 1, 1439.
50. A. Avenoza, C. Cativiela, M. A. Fernandez-Recio, J. M. Peregrina, Tetrahedron: Asymmetry 1999, 10, 3999.
51. I. Cabanal-Duvillard, J.-F. Berrien, J. Royer, H.-P. Husson, Tetrahedron Lett. 1998, 39, 5181.
52. J. W. Bastable, A. J. Copper, I. R. Dunkin, J. D. Hobson, W. D. Riddell, J. Chem. Soc., Perkin Trans. 1 1981, 1339.
53. M. E. Maier, T. Lapeva, Synlett 1998, 891.
54. H. Okumoto, S. Nishihara, S. Yamamoto, H. Hino, A. Nozawa, A. Suzuki, Synlett 2000, 991.
55. J. R. Pfister, W. E. Wymann, Synthesis 1983, 38.
56. P. A. Jacobi, S. Murphree, F. Rupprecht, W. Zheng, J. Org. Chem. 1996, 61, 2413.
57. M. Toyota, M. Yokota, M. Ihara, J. Am. Chem. Soc. 2001, 123, 1856.
58. D. L. Boger, S. H. Kim, Y. Mori, J.-H. Weng, O. Rogel, S. L. Castle, J. J. McAtee, J. Am. Chem. Soc. 2001, 123, 1862.
59. Y. Konda, Y. Takahashi, S. Arima, N. Sato, K. Takeda, K. Dobashi, M. Baba, Y. Harigaya, Tetrahedron 2001, 57, 4311.
60. M.-E. Gourdel-Martin, F. Huet, J. Org. Chem. 1997, 62, 2166.
61. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, M. Lipton, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
62. L. A. Popova, V. I. Biba, V. M. Prishchepenko, S. V. Shavyrin, N. G. Kozlov, J. Gen. Chem. USSR 1993, 67, 1346.
63. R. J. Ryan, S. Julia, Tetrahedron 1973, 29, 3649.
64. A. D. Jones, D. W. Knight, D. E. Hibbs, J. Chem. Soc., Perkin Trans. 1 2001, 1182.
65. A. Avenoza, C. Cativiela, J. M. Peregrina, Tetrahedron 1994, 50, 10021.
66. B. Trupp, H. Fritz, H. Prinzbach, H. Irmgartinger, U. Reifenstahl, Chem. Ber. 1991, 124, 1777.
67. A. G. Griesbeck, H. Heckroth, J. Am. Chem. Soc. 2002, 124, 396.
68. A. Modro, G. H. Schmid, K. Yates, J. Org. Chem. 1977, 42, 3673.
69. G. Bellucci, R. Bianchini, S. Vecchiani, J. Org. Chem. 1986, 51, 4224.
70. G. Bellucci, C. Chiappe, G. Lo Moro, J. Org. Chem. 1997, 62, 3176.
71. A. Boschi, C. Chiappe, A. De Rubertis, M. F. Ruasse, J. Org. Chem. 2000, 65, 8470.
72. P. L. Barili, G. Bellucci, F. Marioni, I. Morelli, V. Scartoni, J. Org. Chem. 1972, 37, 4353.
73. T. J. Donohoe, L. Mitchell, M. J. Waring, M. Helliwell, A. Bell, N. J. Newcombe, Org. Biomol. Chem. 2003, 1, 2173.
74. R. D. Green, Can. J. Chem. 1969, 47, 2407.
75. P. L. Barili, G. Bellucci, G. Berti, M. Golfarini, F. Marioni, V. Scartoni, Gazz. Chim. Ital. 1974, 104, 107.
76. G. Bellucci, G. Berti, R. Bianchini, G. Ingrosso, E. Mastrorilli, Gazz. Chim. Ital. 1976, 106, 955.
77. G. Bellucci, C. Chiappe, F. Marioni, J. Am. Chem. Soc. 1987, 109, 515.
78. P. K. Bakshi, M. A. James, T. S. Cameron, O. Knop, Can. J. Chem. 1996, 74, 559.
79. K. N. Robertson, P. K. Bakshi, T. S. Cameron, O. Knop, Z. Anorg. Allg. Chem. 1997, 623, 104.
80. L. Dolci, F. Dolle, H. Valette, F. Vaufrey, C. Fuseau, M. Bottlaender, C. Crouzel, Bioorg. Med. Chem. 1999, 7, 467.
81. B. P. Hart, H. Rapoport, J. Org. Chem. 1999, 64, 2050.
82. G. Bellucci, M. Ferretti, G. Ingrosso, F. Marioni, A. Marsili, I. Morelli, Tetrahedron Lett. 1972, 34, 3527.
83. J. J. Moura Ramos, L. Dumont, L. M. Stien, J. Reisse, J. Am. Chem. Soc. 1980, 102, 4150.
84. L. M. Jackman, S. Sternhell, 'Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry', Pergamon Press, Oxford, 1969.
85. R. Davies, J. Chem. Soc., Perkin Trans. 2 1975, 1400.
86. D. Höfner, S. A. Lesko, G. Binsch, Org. Magn. Reson. 1978, 11, 179.
87. P. Kapferer, V. Birault, J.-F. Poisson, A. Vasella, Helv. Chim. Acta 2003, 86, 2210.