Study of a radical cyclizations cascade leading to bicyclo[3.1.1]heptanes

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 819-825

  Bogen, Stéphane ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.1.1]HEPTANE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; DRUG CONFORMATION; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0033525025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981622u     Document Type: Article

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48. Merényi, Janousek and Viehe have proposed a relative radical stabilization scale, on which the propargyl radical ranks among the best stabilized radicals, less than allyl but better than benzyl, see: Merényi, R.; Janousek, H. G.; Viehe, H. G. In Substituents Effects in Radical Chemistry; Viehe, H. G., Janousek, H. G., Merényi, R. D., Eds.; Reidel Publishing Co.: Louvain-la-Neuve, Belgium, 1986; p 315. See also: (a) Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062. (b) Engel, P. S.; Dalton, A. I.; Shen, L. J. Org. Chem. 1974, 39, 384.
49. Merényi, Janousek and Viehe have proposed a relative radical stabilization scale, on which the propargyl radical ranks among the best stabilized radicals, less than allyl but better than benzyl, see: Merényi, R.; Janousek, H. G.; Viehe, H. G. In Substituents Effects in Radical Chemistry; Viehe, H. G., Janousek, H. G., Merényi, R. D., Eds.; Reidel Publishing Co.: Louvain-la-Neuve, Belgium, 1986; p 315. See also: (a) Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062. (b) Engel, P. S.; Dalton, A. I.; Shen, L. J. Org. Chem. 1974, 39, 384.
50. Merényi, Janousek and Viehe have proposed a relative radical stabilization scale, on which the propargyl radical ranks among the best stabilized radicals, less than allyl but better than benzyl, see: Merényi, R.; Janousek, H. G.; Viehe, H. G. In Substituents Effects in Radical Chemistry; Viehe, H. G., Janousek, H. G., Merényi, R. D., Eds.; Reidel Publishing Co.: Louvain-la-Neuve, Belgium, 1986; p 315. See also: (a) Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062. (b) Engel, P. S.; Dalton, A. I.; Shen, L. J. Org. Chem. 1974, 39, 384.
51. 4-exo-dig radical cyclizations are unfavorable according to Baldwin's rules and to our knowledge have not been observed: Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
52. Kinetics: (a) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Perkin Trans. 2 1980, 1083.
53. (b) Ingold, K. U.; Maillard, B.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1981, 970.
54. (a) Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett. 1991, 32, 2235.
55. (b) Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276.
56. (a) Park, S.-U.; Varick, T. R.; Newcomb, M. Tetrahedron Lett. 1990, 31, 2975.
57. (b) Jung, M. E.; Trifunovich, I. D.; Lensen, N. Tetrahedron Lett. 1992, 33, 6179. For a discussion of gem-disubstituted effects, see: Jung, M. E.; Marquez, R. Tetrahedron Lett 1997, 38, 6521.
58. (b) Jung, M. E.; Trifunovich, I. D.; Lensen, N. Tetrahedron Lett. 1992, 33, 6179. For a discussion of gem-disubstituted effects, see: Jung, M. E.; Marquez, R. Tetrahedron Lett 1997, 38, 6521.
59. (a) Gill, G. B.; Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1989, 30, 3229.
60. (b) Quiclet-Sire, B.; Saunier, J. B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 1397.
61. For a recent discussion on this topic, see: Manabe, T.; Yanagi, S.-i.; Ohe, K.; Uemura, S. Organometallics 1998, 17, 2942.
62. The use of propargyl radicals is very limited, see: (a) Quiclet-Sire, B.; Zard, S, Z. J. Am. Chem. Soc. 1996, 118, 1209. (b) Denieul, M.-P.; Quiclet-Sire, B.; Zard, S, Z. Tetrahedron Lett. 1996, 37, 5495. (c) Wartenberg, F.-H.; Junga, H.; Blechert, S. Tetrahedron Lett. 1993, 34, 5251. (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr., Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
63. The use of propargyl radicals is very limited, see: (a) Quiclet- Sire, B.; Zard, S, Z. J. Am. Chem. Soc. 1996, 118, 1209. (b) Denieul, M.-P.; Quiclet-Sire, B.; Zard, S, Z. Tetrahedron Lett. 1996, 37, 5495. (c) Wartenberg, F.-H.; Junga, H.; Blechert, S. Tetrahedron Lett. 1993, 34, 5251. (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr., Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
64. The use of propargyl radicals is very limited, see: (a) Quiclet- Sire, B.; Zard, S, Z. J. Am. Chem. Soc. 1996, 118, 1209. (b) Denieul, M.-P.; Quiclet-Sire, B.; Zard, S, Z. Tetrahedron Lett. 1996, 37, 5495. (c) Wartenberg, F.-H.; Junga, H.; Blechert, S. Tetrahedron Lett. 1993, 34, 5251. (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr., Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
65. The use of propargyl radicals is very limited, see: (a) Quiclet- Sire, B.; Zard, S, Z. J. Am. Chem. Soc. 1996, 118, 1209. (b) Denieul, M.-P.; Quiclet-Sire, B.; Zard, S, Z. Tetrahedron Lett. 1996, 37, 5495. (c) Wartenberg, F.-H.; Junga, H.; Blechert, S. Tetrahedron Lett. 1993, 34, 5251. (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr., Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
66. Salazar, K. L.; Khan, M. A.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 9053.
67. For related exclusive 6-endo-trig cyclizations: (a) Satoh, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1991, 56, 2278. (b) Pal, S.; Mukherjee, M.; Podder, D.; Mukherjee, A. K.; Ghatak, U. R. J. Chem. Soc., Chem. Commun. 1991, 1591.
68. For related exclusive 6-endo-trig cyclizations: (a) Satoh, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1991, 56, 2278. (b) Pal, S.; Mukherjee, M.; Podder, D.; Mukherjee, A. K.; Ghatak, U. R. J. Chem. Soc., Chem. Commun. 1991, 1591.
69. 1 and the axial methyl groups. pseudo-chair, face β, 35βc (equation presented)
70. In a general study of the 5-endo-trig cyclization, we have shown that vinyl radicals of type 52 are completely reduced in an intramolecular fashion through a chemoselective 1,5-H transfer: Bogen, S.; Fensterbank, L.; Malacria, M. To be published.
71. We cannot rule out that 53 directly originates from vinyl radical 58. However, previous work in our laboratory suggests that vinyl radical of type 58 is highly protected against intermolecular reduction (see also note 28).
72. Still, W.; Kahn, M.; Mittra, A. J. Org. Chem. 1978, 43, 2923.