Asymmetric synthesis of tropanes by rhodium-catalyzed [4 + 3] cycloaddition

Journal of the American Chemical Society

Volumn 129, Issue 34, 2007, Pages 10312-10313

  Reddy, Ravisekhara P ^a   Davies, Huw M L ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; RHODIUM; TROPANE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY;

CATALYSIS; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM; TROPANES;

EID: 34548219536     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072936e     Document Type: Article

References (31)

1. (a) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
2. (b) O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637.
3. (c) Fodor, G.; Dharanipragada, R. Nat. Prod. Rep. 1994, 11, 443.
4. (d) Lounasmaa, M.; Tamminen, T. In The Tropane Alkaloids in Alkaloids; Academic Press: New York, 1993; Vol. 44, pp 1-114.
5. Singh, S. Chem. Rev. 2000, 100, 925.
6. (a) Willstatter, R. Ber. 1896, 29, 936.
7. (b) Willstatter, R. Liebigs Ann. Chem. 1903, 326, 23.
8. (c) Robinson, R. J. Chem. Soc. 1917, 111, 762.
9. (a) Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207.
10. (b) Armstrong, A.; Shanahan, S. E. Org. Lett. 2005, 7, 1335.
11. (c) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469.
12. (d) Malinakova, H. C.; Liebeskind, L. S. Org. Lett. 2000, 2, 3909.
13. (e) Lin, R.; Castells, J.; Rapoport, H. J. Org. Chem. 1998, 63, 4069.
14. (a) Antoline, J. E.; Hsung, R. P.; Huang, J.; Song, Z.; Li, G. Org. Lett. 2007, 9, 1275.
15. (b) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50.
16. (c) Xiong, H.; Huang, J.; Ghosh, S. K.; Hsung, R. P. J. Am. Chem. Soc. 2003, 125, 12694.
17. (d) Cho, S. Y.; Lee, J. C.; Cha, J. K. J. Org. Chem. 1999, 64, 3394.
18. (e) Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930.
19. 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.
20. Davies, H. M. L.; Peng, Z.-Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939.
21. Davies, H. M. L. Eur. J. Org. Chem. 1999, 9, 2459.
22. Müller, P.; Bernardinelli, G.; Allenbach, Y. F.; Ferri, M.; Flack, H. D. Org. Lett. 2004, 6, 1725.
23. (a) Reddy, R. P.; Lee, G.; Davies, H. M. L. Org. Lett. 2006, 8, 3437.
24. (b) Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625.
25. Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. S. Tetrahedron Lett. 1998, 39, 4417.
26. Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S.-I. Synlett 1996, 85.
27. Davies, H. M. L.; Gilliat, V.; Kuhn, L.; Saikali, E.; Ren, P.; Hammond, P. S.; Sexton, T.; Childers, S. R. J. Med. Chem. 2001, 44, 1509.
28. (a) Katoh, T.; Kakiya, K.; Nakai, T.; Nakamura, S.; Nishide, K.; Node, M. Tetrahedron: Asymmetry 2002, 13, 2351.
29. (b) Hernandez, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
30. Hedley, S. J.; Ventura, D. L.; Dominiak, P. M.; Nygren, C. L.; Davies, H. M. L. J. Org. Chem. 2006, 71, 5349.
31. Kende, A. S.; Smalley, T. L., Jr.; Huang, H. J. Am. Chem. Soc. 1999, 121, 7431.