Synthesis of enantiopure azetidines: A route to new β-amino alcohols

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 8023-8025

  De Talancé, Vincent Lemau ^a   Banide, Emilie ^a   Bertin, Benjamin ^a   Comesse, Sébastien ^a,b   Kadouri Puchot, Catherine ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ DU HAVRE   (France)

Author keywords

Amino alcohols; Azetidines; N Bromosuccinimide; Vinylbromide; Vinylsilane

Indexed keywords

ALCOHOL DERIVATIVE; AZETIDINE DERIVATIVE; N BROMOSUCCINIMIDE; SILANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; STEREOISOMERISM;

EID: 26844565066     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.061     Document Type: Article

References (38)

1. For reviews, see: N. De Kimpe A. Padwa Comprehensive Heterocyclic Chemistry II Vol. 1B 1996 Elsevier Oxford 507 589 Chapter 1.18
2. F. Couty, G. Evano, and D. Prim Mini-Rev Org. Chem. 1 2004 133
3. Selected recent examples of asymmetric synthesis of azetidines: R. Pedrosa, C. Andrés, J. Nieto, and S. del Pozo J. Org. Chem. 70 2005 1408
4. S. Mangelinckx, M. Boeykens, M. Vliegen, J. Van der Eycken, and N. De Kimpe Tetrahedron Lett. 46 2005 525
5. D. Enders, J. Gries, and Z.-S. Kim Eur. J. Org. Chem. 2004 4471
6. F. Couty, G. Evano, and N. Rabasso Tetrahedon: Asymmetry 14 2003 2407
7. A.C.B. Burtoloso, and C.R.D. Correia Tetrahedron Lett. 45 2004 3355
8. For azetidines used as ligands, see for example: W.A.J. Starmans, R.W.A. Walgers, L. Thijs, R. de Gelder, J.M.M. Smits, and B. Zwanenburg Tetrahedron 54 1998 4991
9. M. Shi, and J.-K. Jiang Tetrahedron: Asymmetry 10 1999 1673
10. P.J. Hermsen, J.G.O. Cremers, L. Thijs, and B. Zwanenburg Tetrahedron Lett. 42 2001 4243
11. J. Wilken, S. Erny, S. Wassmann, and J. Martens Tetrahedron: Asymmetry 11 2000 2143
12. F. Couty, and D. Prim Tetrahedron: Asymmetry 13 2002 2619
13. L. Keller, M.V. Sanchez, D. Prim, F. Couty, G. Evano, and J. Marrot J. Organomet. Chem. 690 2005 2306
14. For azetidines as components in natural products, see, for example: T. Akihisa, S. Mafune, M. Ukiya, Y. Kimura, K. Yasukawa, T. Suzuki, H. Tokuda, N. Tanabe, and T. Fukuoka J. Nat. Prod. 67 2004 479
15. H. Takikawa, T. Maeda, M. Seki, H. Koshino, and K. Mori J. Chem. Soc., Perkin Trans. 1 1997 97
16. H. Yoda, T. Uemura, and K. Takabe Tetrahedron Lett. 44 2003 977
17. S. Singh, G. Crossley, S. Ghosal, Y. Lefievre, and M.W. Pennington Tetrahedron Lett. 46 2005 1419
18. For synthesis and biological activities of some azetidines derivatives, see for example: J. Frigola, A. Torrens, J.A. Castrillo, J. Mas, D. Vañó, J.M. Berrocal, C. Calvet, L. Salgado, J. Redondo, S. García-Granda, E. Valentí, and J.R. Quintana J. Med. Chem. 37 1994 4195
19. S.L. Lautar, C. Rojas, B.S. Slusher, K.M. Wozniak, Y. Wu, A.G. Thomas, D. Waldon, W. Li, D. Ferraris, and S. Belyakov Brain Res. 1048 2005 177
20. M.M. Morrissette, K.J. Stauffer, P.D. Williams, T.A. Lyle, J.P. Vacca, J.A. Krueger, S.D. Lewis, B.J. Lucas, B.K. Wong, R.B. White, C. Miller-Stein, E.A. Lyle, A.A. Wallace, Y.M. Leonard, D.C. Welsh, J.J. Lynch, and D.R. McMasters Bioorg. Med. Chem. Lett. 14 2004 4161
21. A.P. Kozikowski, W. Tückmantel, I.J. Reynolds, and J.T. Wroblewski J. Med. Chem. 33 1990 1561
22. W.-L. Wu, M.A. Caplen, M.S. Domalski, H. Zhang, A. Fawzi, and D.A. Burnett Bioorg. Med. Chem. Lett. 12 2002 3157
23. S. Hanessian, N. Bernstein, R.-Y. Yang, and R. Maguire Bioorg. Med. Chem. Lett. 9 1999 1437
24. Q. Cheng, H. Kiyota, M. Yamaguchi, T. Horiguchi, and T. Oritani Bioorg. Med. Chem. Lett. 13 2003 1075
25. N. De Kimpe, and D. De Smaele J. Heterocyclic Chem. 37 2000 607
26. X. Pannecoucke, F. Outurquin, and C. Paulmier Eur. J. Org. Chem. 2002 995
27. F. Outurquin, X. Pannecoucke, B. Berthe, and C. Paulmier Eur. J. Org. Chem. 2002 1007
28. C. Agami, S. Comesse, and C. Kadouri-Puchot J. Org. Chem. 67 2002 2424
29. C. Agami, S. Comesse, S. Guesné, C. Kadouri-Puchot, and L. Martinon Synlett 2003 1058
30. C. Agami, S. Comesse, and C. Kadouri-Puchot J. Org. Chem. 67 2002 1496
31. B. Berthe, F. Outurquin, and C. Paulmier Tetrahedron Lett. 38 1997 1393
32. Atomic coordinates, bond lengths and angles and thermal parameters have been deposited at the Cambridge Crystallographical Data Center with the deposition number CCDC 277622.
33. 32BrNOSi: C, 57.27; H, 8.09; N, 3.52. Found: C, 57.33; H, 8.23; N, 3.41.
34. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734
35. J.B. Lambert, Y. Zhao, R.W. Emblidge, L.A. Salvador, X. Liu, J.-H. So, and E.C. Chelius Acc. Chem. Res. 32 1999 183
36. A similar silicon-directed 4-exo-trig electrophilic cyclization of homoallylic alcohols led to the formation of oxetanes: M. Rofoo, M.-C. Roux, and G. Rousseau Tetrahedron Lett. 42 2001 2481
37. 22NOBr: C, 57.70; H, 7.10; N, 4.49. Found: C, 58.19; H, 7.40; N, 4.34.
38. A stereospecific anti elimination of β-silyl azides has been reported: L. Chabaud, and Y. Landais Tetrahedron Lett. 44 2003 6995