Tandem asymmetric cyclopropanation/Cope rearrangement. A highly diastereoselective and enantioselective method for the construction of 1,4- cycloheptadienes

Journal of the American Chemical Society

Volumn 120, Issue 14, 1998, Pages 3326-3331

  Davies, Huw M L ^a   Stafford, Douglas G ^a   Doan, Brian D ^a   Houser, Jeffrey H ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEPTADIENE; ALKADIENE; CYCLOPROPANE; RHODIUM (N DODECYLBENZENESULFONYL)PROLINATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DECOMPOSITION; DRUG SYNTHESIS; GENE REARRANGEMENT; MOLECULAR INTERACTION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TANDEM REPEAT;

EID: 0032522284     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja974201n     Document Type: Article

References (60)

1. For general reviews on the Cope rearrangement of divinylcyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (b) Rhoads, S. J.; Raulinus, N. R. Org. React. 1975, 21, 1. (c) Hudlicky, T.: Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org React. 1992, 41, 1. (d) Piers, E. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 971-998.
2. For general reviews on the Cope rearrangement of divinylcyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (b) Rhoads, S. J.; Raulinus, N. R. Org. React. 1975, 21, 1. (c) Hudlicky, T.: Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org React. 1992, 41, 1. (d) Piers, E. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 971-998.
3. For general reviews on the Cope rearrangement of divinylcyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (b) Rhoads, S. J.; Raulinus, N. R. Org. React. 1975, 21, 1. (c) Hudlicky, T.: Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org React. 1992, 41, 1. (d) Piers, E. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 971-998.
4. For general reviews on the Cope rearrangement of divinylcyclopropanes, see: (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (b) Rhoads, S. J.; Raulinus, N. R. Org. React. 1975, 21, 1. (c) Hudlicky, T.: Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org React. 1992, 41, 1. (d) Piers, E. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 971-998.
5. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
6. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
7. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
8. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
9. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
10. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
11. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
12. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
13. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
14. For recent examples of the Cope rearrangement of divinylcyclopropanes, see: (a) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (b) Davies, H. M. L.; Ahmed, G.; Chruchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774. (c) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967. (d) Davies, H. M. L.; Matasi, J. J.; Thornley, C. Tetrahedron Lett. 1995, 36, 7205. (e) Davies, H. M. L.: Calvo, R.; Ahmed G. Tetrahedron Lett. 1997, 38, 1737. (f) Davies, H. M. L.: Matasi J. J.; Ahmed. G. J. Org. Chem. 1996, 61, 2305. (g) Kohmoto, S.; Nakayama, N.; Takami, J.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Tetrahedron Lett. 1996, 37, 7761. (h) Lee, J. H.; Kim, H. J.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. (i) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400. (j) Fukuyama, T., Liu, G. J. Am. Chem. Soc. 1996, 118, 7426.
15. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
16. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
17. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
18. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
19. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
20. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
21. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
22. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
23. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
24. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
25. Other methods for the construction of seven-membered rings include: 3 + 4 annulations: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. (b) Noyori, R. Acc. Chem. Res. 1979, 12, 61. (c) Mann, J. Tetrahedron 1986, 42, 4611. (d) Hosomi, A.; Tominaga, Y. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 593-616. (e) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695. 5 + 2 annulations (f) Wender, P. A.; Lee, H. Y.; Wilheim, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954. (g) Bromidge, S. M.; Archer, D. A.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1990, 353. (h) Dennis, N.; Katritzky, A. R.; Parton, S. K.; Nomura, Y.; Takahashi, Y.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2289. (i) Wender. P. A.; Siggel, L.; Nuss, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 645-674. (j) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114. (k) Marshall, K. A.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9135.
26. For newer annulation methods for the construction of seven-membered rings, see: (a) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877. (c) Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617. (d) Herndon, J. W.; Chatterjee, G.; Patel, M. D.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
27. For newer annulation methods for the construction of seven-membered rings, see: (a) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877. (c) Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617. (d) Herndon, J. W.; Chatterjee, G.; Patel, M. D.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
28. For newer annulation methods for the construction of seven-membered rings, see: (a) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877. (c) Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617. (d) Herndon, J. W.; Chatterjee, G.; Patel, M. D.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
29. For newer annulation methods for the construction of seven-membered rings, see: (a) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877. (c) Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617. (d) Herndon, J. W.; Chatterjee, G.; Patel, M. D.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
30. For newer annulation methods for the construction of seven-membered rings, see: (a) Trost, B. M.; MacPherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483. (b) Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877. (c) Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617. (d) Herndon, J. W.; Chatterjee, G.; Patel, M. D.; Matasi, J. J.; Turner, S. U.; Harp, J. J.; Reid, M. D. J. Am. Chem. Soc. 1991, 113, 7808. (e) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
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