Ring expansion of 2-alkenyl azetidines into unsaturated azocanes

Synlett

Volumn , Issue 19, 2009, Pages 3182-3186

  Drouillat, Bruno ^a   Couty, François ^a   Razafimahaléo, Vanessa ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Azetidines; Azocanes; Ring expansion

Indexed keywords

2 ALKENYL AZETIDINE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMPHOLYTE; AZETIDINE DERIVATIVE; AZOCINE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; HYDROGENATION; PROTON TRANSPORT;

EID: 72049106106     PISSN: 09365214     EISSN: 14372096     Source Type: None    
DOI: 10.1055/s-0029-1218351     Document Type: Article

References (36)

1. For general reviews on the synthesis of azetidines prior to 2000, see: (a) Moore, J. A. In Heterocyclic Compounds with Three and Four-Membered Rings; Weissberger, A., Ed.; Interscience Publishers: New-York, 1964, Part 2, 885-977.
2. (b) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331.
3. Moore, J. A.; Ayers, R. S. In Small Ring HeterocyclesPart 2-Azetidines, ß-Lactams, Diazetidines, and Diaziridines; Hassner, A., Ed.; John Wiley and Sons, Inc.: New York, 1983, 1.
4. De Kimpe, N. Azetidines, Azetines and Azete, In Comprehensive Heterocyclic Chemistry II, a review of the Literature of 1982-1995, Vol.IB; Pergamon: Oxford, 1996. For more recent reviews, see:
5. (e)Dejaegher, Y.; Kuz'menok, N. M.; Zvonok, A. M.; De Kimpe, N. Chem. Rev. 2002,102, 29.
6. (f) Couty, F.; Evano, G.; Prim, D. MiniRev. Org. Chem. 2004,1, 133.
7. (g) Couty, F.; Evano, G. Org. Prep. Proced. Int. 2006,38, 427.
8. (h) Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008,108, 3988.
9. Couty, F. Synthesis of Azetidines, In Science of Synthesis: HoubenWeyl Methods of Molecular Transformations, Vol.40a; Enders, D., Ed.; Georg Thieme Verlag: New York, 2009, 773-817.
10. Padwa, A.; Gruber, R. J. Am. Chem. Soc. 1970, 92, 107.
11. Roberto, D.; Alper, H. J. Am. Chem. Soc. 1989,111, 7539.
12. (a) Durrat, F.; Vargas-Sanchez, M.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 3286.
13. (b) Drouillat, B.; Couty, F.; David, O.; Evano, G.; Marrot, J. Synlett 2008, 1345.
14. Van Bradandt, W.; Van Landeghem, R.; De Kimpe, N. Org. Lett. 2006, 8, 1105.
15. Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Chem. Commun. 2001, 958.
16. Couty, F.; Durrat, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2006, 4214.
17. For a review on this topic, see: Couty, F.; Durrat, F.; Evano, G. Targets in Heterocyclic Systems-Chemistry and Properties, Vol.9; Attanasi, O. A.; Spinelu, D., Eds.; Italian Society of Chemistry: Rome, 2005, 186.
18. Weston, M. H.; Nakajima, K.; Parvez, M.; Back, T. G. Chem. Commun. 2006, 3903.
19. Weston, M. H.; Nakajima, K.; Back, T. G. J. Org. Chem. 2008, 73, 4630.
20. Winnick, M. A. Chem. Rev. 1981, 81,491.
21. For examples of macrocyclisation involving N-alkylation, see (a) Kan, T.; Fujiwara, A.; Kobayashi, H.; Fukuyama, T. Tetrahedron 2002, 58, 6267.
22. (b) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991.
23. Sattely, E. S.; Cortez, G. A.; Moebius, D. C.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 8526. For examples of RCM, see:
24. Gille, S.; Ferry, A.; Billard, T.; Langlois, B. R. J. Org. Chem. 2003, 68, 8932. For examples of ring cleavage, see:
25. (e) Vedejs, E.; Galante, R. J.; Goekjian, P. G. J. Am. Chem. Soc. 1998,120, 3613.
26. (f) Iradier, F.; Arrayas, R. G.; Carretero, C. Org. Lett. 2001, 3, 2957.
27. (g) For examples of rearrangement, see: MaGee, D. I.; Beck, E. J. J. Org. Chem. 2000, 65, 8367.
28. For examples of [2,3]-sigmatropic shifts, see: (h) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
29. Voskressensky, L. G.; Listratova, A. V.; Borisova, T. N.; Kovaleva, S. A.; Borisov, R. S.; Varlamov, A. V. Tetrahedron 2008, 64, 10443.
30. White, J. D. J. Org. Chem. 2000, 65, 9129; See also ref. 11e.
31. (a) Godin, G.; Garnier, E.; Compain, P.; Martin, O. R.; Ikeda, K.; Asano, N. Tetrahedron Lett. 2004, 45, 579.
32. (b) Chang, M.-Y.; Kung, Y.-H.; Ma, C.-C; Chen, S.-T. Tetrahedron 2007, 63, 1339.
33. Couty, F.; Prim, D. Tetrahedron: Asymmetry 2006,13, 2619.
34. Walters, M. A. J. Org. Chem. 1996, 61, 978.
35. Ramachandran, P. V.; Rudd, M. T.; Reddy, M. R. Tetrahedron Lett. 2005,46, 2547.
36. +].