Rearrangement of 2-hydroxyalkylazetidines into 3-fluoropyrrolidines

Synlett

Volumn , Issue 9, 2008, Pages 1345-1348

  Drouillat, Bruno ^a   Couty, François ^a   David, Olivier ^a   Evano, Gwilherm ^a   Marrot, Jérome ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

Azetidines; DAST; Fluorination; Pyrrolidines

Indexed keywords

ANION; AZETIDINE DERIVATIVE; FLUORIDE; PENTANE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 45749106438     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072770     Document Type: Article

References (31)

1. Humphreys, A. Med Ad News 2006, 25 (6), 20.
2. (a) Demange, L.; Ménez, A.; Dugave, C. Tetrahedron Lett. 1998, 39, 1169; and references cited therein.
3. (b) Singh, R. P.; Shreeve, J. M. J. Fluorine Chem. 2002, 116, 23.
4. (c) Burger, K.; Rudolph, M.; Fehn, S.; Sewald, N. J. Fluorine Chem. 1994, 66, 87.
5. (a) Hulin, B.; Cabral, S.; Lopaze, M. G.; Van Volkenburg, M. A.; Andrews, K. M.; Parker, J. C. Bioorg. Med. Chem. Lett. 2005, 15, 4770.
6. (b) Ayad, T.; Génisson, Y.; Broussy, S.; Baltas, M.; Gorrichon, L. Eur. J. Org. Chem. 2003, 2903.
7. Xu, F.; Simmons, B.; Armstrong, J., III; Murry, J. J. Org. Chem. 2005, 70, 6105.
8. Bonini, F. B.; Boschi, F.; Franchini, M. C.; Fochi, M.; Fini, F.; Mazzanti, A.; Ricci, A. Synlett 2006, 543.
9. Li, Y.; Hu, J. Angew. Chem. Int. Ed. 2007, 46, 2489.
10. Smith, E. M.; Swiss, G. F.; Neustadt, B. R.; Gold, E. H.; Sommer, J. A.; Brown, A. D.; Chiu, P. J. S.; Moran, R.; Sybertz, E. J.; Baum, T. J. Med. Chem. 1988, 31, 875.
11. Inagaki, H.; Miyauchi, S.; Miyauchi, R. N.; Kawato, H. C.; Ohki, H.; Matsuhachi, N.; Kawakami, K.; Takahashi, H.; Takemura, M. J. Med. Chem. 2003, 46, 1005.
12. Yang, W.; Wang, Y.; Roberge, J. Y.; Ma, Z.; Liu, Y.; Lawrence, R. M.; Rotella, D. P.; Seethala, R.; Feyen, J. H. M.; Dickson, J. K., Jr. Bioorg. Med. Chem. Lett. 2005, 15, 1225.
13. (a) Xu, J.; Wei, L.; Mathwink, R.; He, J.; Park, Y.-J.; He, H.; Leiting, B.; Lyons, K. A.; Marsillo, F.; Patel, R. A.; Wu, J. K.; Thornberry, N. A.; Weber, A. E. Bioorg. Med. Chem. Lett. 2005, 15, 2533.
14. (b) Ganelin, C. B.; Bisop, P. B.; Bambal, R. B.; Chan, S. M. T.; Leblond, B.; Moore, A. N. J.; Zhao, L.; Bourgeat, P.; Rose, C.; Vargas, F.; Schwartz, J.-C. J. Med. Chem. 2005, 48, 7333.
15. (c) Caldwell, C. G.; Chen, P.; He, J.; Parmee, E. R.; Leiting, B.; Marsilio, F.; Patel, R. A.; Wu, J. K.; Eiermann, G. J.; Petrov, A.; He, H.; Lyons, K. A.; Thornberry, N. A.; Weber, A. E. Bioorg. Med. Chem. Lett. 2004, 14, 1265.
16. O'Neil, I. A.; Thompson, S.; Kalindjan, B.; Jenkins, T. Tetrahedron Lett. 2003, 44, 7809.
17. (a) Déchamps, I.; Gomez Pardo, D.; Cossy, J. Synlett 2007, 263.
18. (b) Déchamps, I.; Gomez Pardo, D.; Cossy, J. Eur. J. Org. Chem. 2007, 4224.
19. (a) Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209.
20. (b) Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 7, 5861.
21. (c) Couty, F.; Durrat, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2006, 4214.
22. (a) Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297.
23. (b) Couty, F.; Prim, D. Tetrahedron: Asymmetry 2002, 13, 2619.
24. (c) Couty, F.; Durrat, F.; Evano, G.; Prim, D. Tetrahedron Lett. 2004, 45, 7525.
25. (d) Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem. 2005, 70, 9028.
26. (e) Couty, F.; Evano, G.; Rabasso, N. Tetrahedron: Asymmetry 2003, 14, 2407.
27. Middleton, W. J. J. Org. Chem. 1975, 40, 574.
28. Crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 676883.
29. The kinetic control invoked here is also supported by the chemical stability of 36, which does not rearrange when heated at 100°C in toluene for 8 h.
30. +].
31. Couty, F.; Durrat, F.; Evano, G. Targets in Heterocyclic Systems - Chemistry and Properties, Vol. 9; Attanasi, O. A.; Spinelli, D., Eds.; Italian Society of Chemistry: Rome, 2005, 186.