Intramolecular carbolithiation reactions for the preparation of azabicyclo [2.2.1] heptanes

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3788-3795

  Coldham, Iain ^a   Fernàndez, Joan Carles ^a   Price, Kathy N ^a   Snowden, David J ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HEXAMETHYLENEIMINE DERIVATIVE; LITHIUM; NORBORNANE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 6044229609     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000088z     Document Type: Article

References (43)

1. For an example, see: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 4353.
2. (a) Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F. J. J. Am. Chem. Soc. 1998, 120, 4865.
3. (b) Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett 1998, 930.
4. (c) Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248.
5. (d) Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594.
6. (e) Bailey, W. F.; Jiang, X.-L. J. Org. Chem. 1996, 61, 2596.
7. (a) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617.
8. (b) Coldham, I.; Hufton, R. Tetrahedron 1996, 52, 12541.
9. (c) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954.
10. (d) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981.
11. (a) Woltering, M. J.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1764.
12. (b) Ahmed, A.; Clayden, J.; Rowley, M. Tetrahedron Lett. 1998, 39, 6103.
13. (c) Woltering, M. J.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synlett 1998, 797.
14. (d) Tomooka, K.; Komine, N.; Sasaki, T.; Shimizu, H.; Nakai, T. Tetrahedron Lett. 1998, 39, 9715.
15. Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
16. Coldham, I.; Fernàndez, J.-C.; Snowden, D. J. Tetrahedron Lett. 1999, 40, 1819.
17. Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K.; Ovaska, T. V.; Rossi, K.; Thiel, Y.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 5720.
18. Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
19. Gawley, R. E.; Zhang, Q.; Campagna, S. J. Am. Chem. Soc. 1995, 117, 11817.
20. Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
21. Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1997, 38, 8939.
22. Beak, P.; Lee W. K. J. Org. Chem. 1993, 58, 1109.
23. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
24. Boeckman, R. K.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
25. Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Org. Chem. 1996, 61, 7627.
26. (a) Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201.
27. (b) Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842.
28. (c) Pearson, W. H.; Lindbeck, A. C. J. Am. Chem. Soc. 1991, 113, 8546.
29. (d) Weisenburger, G. A.; Faibish, N. C.; Pippel, D. J.; Beak, P. J. Am. Chem. Soc. 1999, 121, 9522.
30. Amano, S.; Fujiwara, K.; Murai, A. Chem. Lett. 1998, 409.
31. Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183.
32. Zablocki, J. A.; Rico, J. G.; Garland, R. B.; Rogers, T. E.; Williams, K.; Schretzman, L. A.; Rao, S. A.; Bovy, P. R.; Tjoeng, F. S.; Lindmark, R. J.; Toth, M. V.; Zupec, M. E.; McMacins, D. E.; Adams, S. P.; Markos, M. M. C. S.; Milton, M. N.; Paulson, S.; Herin, M.; Jacqmin, P.; Nicholson, N. S.; Panzer-Knodle, S. G.; Haas, N. F.; Page, J. D.; Szalony, J. A.; Taite, B. B.; Salyers, A. K.; King, L. W.; Campion, J. G.; Faigen, L. P. J. Med. Chem. 1993, 38, 2378.
33. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
34. (a) Seyferth, D.; Andrews, S. B. J. Organomet. Chem. 1971, 30, 151.
35. (b) Seitz, D. E.; Carroll, J. J.; Cartaya, C. P.; Lee, S.-H.; Zapata, A. Synth. Commun. 1983, 13, 129.
36. (c) Ahman, J.; Somfai, P. Synth. Commun. 1994, 24, 1117.
37. Jung, M. E.; Blum, R. B. Tetrahedron Lett. 1977, 3791.
38. Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053.
39. Pearson, W. H.; Stevens E. P. J. Org. Chem. 1998, 63, 9812.
40. Boche, G.; Marsch, M.; Harbach, J.; Harms, K.; Ledig, B.; Schubert, F.; Lohrenz, J. C. W.; Ahlbrecht, H. Chem. Ber. 1993, 126, 1887.
41. N coordination, although this product is formed only in the presence of TMEDA, which may affect the extent of such coordination.
42. Bailey, W. F.; Khanolkar, A. D. Organometallics, 1993, 12, 239.
43. Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E.; Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621.