Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: Formal syntheses of natural epibatidine and its enantiomer

Tetrahedron Asymmetry

Volumn 14, Issue 20, 2003, Pages 3173-3176

  Moreno Vargas, Antonio J ^a   Vogel, Pierre ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EPIBATIDINE; ETHYLENEDIAMINE DERIVATIVE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CIRCULAR DICHROISM; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; HYDROLYSIS; MOLECULAR INTERACTION; PRIORITY JOURNAL;

EID: 1442317045     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.021     Document Type: Article

References (30)

1. For reviews on the 'naked sugars' methodology and applications, see: (a) Vogel, P. Curr. Org. Chem. 2000, 4, 455-580; (b) Vogel, P. In Glycoscience, Chemistry and Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. II, Chapter 4.4, pp. 1023-1174; (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185; (d) Vogel, P.; Auberson, Y.; Bimwala, M.; de Guchteneere, E.; Vieiera, E.; Wagner, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D.; Hawkins, L. D.; McGarvey, G. L., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; pp. 197-241.
2. For reviews on the 'naked sugars' methodology and applications, see: (a) Vogel, P. Curr. Org. Chem. 2000, 4, 455-580; (b) Vogel, P. In Glycoscience, Chemistry and Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. II, Chapter 4.4, pp. 1023-1174; (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185; (d) Vogel, P.; Auberson, Y.; Bimwala, M.; de Guchteneere, E.; Vieiera, E.; Wagner, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D.; Hawkins, L. D.; McGarvey, G. L., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; pp. 197-241.
3. For reviews on the 'naked sugars' methodology and applications, see: (a) Vogel, P. Curr. Org. Chem. 2000, 4, 455-580; (b) Vogel, P. In Glycoscience, Chemistry and Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. II, Chapter 4.4, pp. 1023-1174; (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185; (d) Vogel, P.; Auberson, Y.; Bimwala, M.; de Guchteneere, E.; Vieiera, E.; Wagner, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D.; Hawkins, L. D.; McGarvey, G. L., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; pp. 197-241.
4. For reviews on the 'naked sugars' methodology and applications, see: (a) Vogel, P. Curr. Org. Chem. 2000, 4, 455-580; (b) Vogel, P. In Glycoscience, Chemistry and Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. II, Chapter 4.4, pp. 1023-1174; (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185; (d) Vogel, P.; Auberson, Y.; Bimwala, M.; de Guchteneere, E.; Vieiera, E.; Wagner, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D.; Hawkins, L. D.; McGarvey, G. L., Eds.; ACS Symposium Series 386; American Chemical Society: Washington, DC, 1989; pp. 197-241.
5. Vieira E., Vogel P. Helv. Chim. Acta. 66:1983;1865-1871.
6. Zhang C., Ballay C.J. II, Trudell M.L. J. Chem. Soc., Perkin Trans. 1. 1999;675-676.
7. Wei Z.-L., George C., Kozikowski A.P. Tetrahedron Lett. 44:2003;3847-3850.
8. Abe H., Arai Y., Aoyagi S., Kibayashi C. Tetrahedron Lett. 44:2003;2971-2973.
9. Wei Z.-L., Petukhov P.A., Xiao Y., Tückmantel W., George C., Kellar K.J., Kozikowski A.P. J. Med. Chem. 46:2003;921-924.
10. Spand T.F., Garraffo H.M., Edwards M.W., Daly J.W. J. Am. Chem. Soc. 114:1992;3475-3478.
11. Daly J.W., Garraffo H.M., Spande T.F., Decker M.W., Sullivan J.P., Williams M. Nat. Prod. Rep. 17:2000;131-135.
12. Fletcher S.R., Baker R., Chambers M.S., Herbert R.H., Hobbs S.C., Thomas S.R., Vernier H.M., Watt A.P., Ball R.G. J. Org. Chem. 59:1994;1771-1778.
13. Hernández A., Marcos M., Rapoport H. J. Org. Chem. 60:1995;2683-2691.
14. Zhang C., Trudell M.L. J. Org. Chem. 61:1996;7189-7191.
15. Albertini E., Barco A., Benetti S., De Risi C., Pollini G.P., Zanirato V. Tetrahedron. 53:1997;17177-17194.
16. Node M., Nishide K., Fujiwara T., Ichihashi S. Chem. Commun. 1998;2364.
17. Clive D.L.J., Yeh V.S.C. Tetrahedron Lett. 39:1998;4789-4792.
18. Karstens W.F.J., Moolenaar M.J., Rutjes F.P.J.T., Grabowska U., Speckamp W.N., Hiemstra H. Tetrahedron Lett. 40:1999;8629-8632.
19. Avenoza A., Cativiela C., Fernández-Recio M.A., Peregrina J.M. Tetrahedron: Asymmetry. 10:1999;3999-4007.
20. Cabanal-Duvillard I., Berrien J.-F., Royer J. Tetrahedron: Asymmetry. 11:2000;2525-2529.
21. Pandey G., Tiwari S.K., Singh R.S., Mali R.S. Tetrahedron Lett. 42:2001;3947-3949.
22. Albertini E., Barco A., De Risi C., Pollini G.P., Zanirato V. Tetrahedron. 53:1997;17177-17194.
23. Foster A., Kovac T., Mosimann H., Renaud P., Vogel P. Tetrahedron: Asymmetry. 10:1999;567-571.
24. 2 in desulfonylation of β-keto sulfones, see: Molander G.A., Hahn G. J. Org. Chem. 51:1986;1135-1138.
25. Alexakis A., Frutos J.C., Mangeney P. Tetrahedron: Asymmetry. 4:1993;2431-2434.
26. For an example of this use, see: Mase N., Watanabe Y., Ueno Y., Toru T. J. Org. Chem. 62:1997;7794-7800.
27. Corey E.J., Pikul S. Org. Synth. 71:1993;22-29.
28. Corey E.J., Lee D.H., Sarsshar S. Tetrahedron: Asymmetry. 6:1995;3-6.
29. Cossu S., De Lucchi O., Pasetto P. Angew. Chem.,Int. Ed. 36:1997;1504-1506.
30. Carrupt P.-A., Vogel P. Tetrahedron Lett. 22:1981;4721-4722.