Transformation of trans -4-aryl-3-chloro-1-(2-chloroethyl)azetidin-2-ones into 3-aryl-2-(ethylamino)propan-1-ols via intermediate 1-(1-aryl-2-chloro-3- hydroxypropyl)aziridines and trans -2-aryl-3-(hydroxymethyl)aziridines

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 264-269

  Mollet, Karen ^a   D'Hooghe, Matthias ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; CYCLOCONDENSATION; DIASTEREOSELECTIVE; RING OPENING;

METHANOL;

ORGANIC COMPOUNDS;

AZETIDINE DERIVATIVE; AZIRIDINE DERIVATIVE; IMINE; LITHIUM DERIVATIVE; PROPANOL; TETRAHYDROFURAN;

ARTICLE; CHEMICAL REACTION; POLYMERIZATION; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

AZETIDINES; AZIRIDINES; IMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 78650882623     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1020932     Document Type: Article

References (48)

1. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159
2. Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467
3. Lait, S. M.; Rankic, D. A.; Keay, B. A. Chem. Rev. 2007, 107, 767
4. Sutcliffe, O. B.; Bryce, M. R. Tetrahedron: Asymmetry 2003, 14, 2297
5. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835
6. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151
7. Hansteen, V.; Moinichen, E.; Lorentsen, E.; Andersen, A.; Strom, O.; Soiland, K.; Dyrbekk, D.; Refsum, A. M.; Tromsdal, A.; Knudsen, K.; Eika, C.; Bakken, J.; Smith, P.; Hoff, P. I. Brit. Med. J. 1982, 284, 155
8. Narimatsu, S.; Arai, T.; Watanabe, T.; Masubuchi, Y.; Horie, T.; Suzuki, T.; Ishikawa, T.; Tsutsui, M.; Kumagai, Y.; Cho, A. K. Chem. Res. Toxicol. 1997, 10, 289
9. Aubriot, S.; Nicolle, E.; Lattier, M.; Morel, C.; Cao, W.; Daniel, K. W.; Collins, S.; Leclerc, G.; Faure, P. Bioorg. Med. Chem. Lett. 2002, 12, 209
10. Dasbiswas, A.; Shinde, S.; Dasbiswas, D. J. Indian Med. Assoc. 2008, 106, 259
11. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837
12. De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1996; Vol. 1B, p 507.
13. Singh, G. S.; D'hooghe, M.; De Kimpe, N. In Comprehensive Heterocyclic Chemistry III; Elseviere Science: New York, 2008; Vol. 2, p 1.
14. Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377
15. Alcaide, B.; Almendros, P. Synlett 2002, 381
16. Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Chem. Rev. 2005, 105, 395
17. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437
18. Ojima, I. Acc. Chem. Res. 1995, 28, 383
19. Singh, G. S. Tetrahedron 2003, 59, 7631
20. D'hooghe, M.; Dekeukeleire, S.; Leemans, E.; De Kimpe, N. Pure Appl. Chem. 2010, 82, 1749
21. Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915
22. Dekeukeleire, S.; D'hooghe, M.; Törnroos, K. W.; De Kimpe, N. J. Org. Chem. 2010, 75, 5934
23. Van Brabandt, W.; De Kimpe, N. J. Org. Chem. 2005, 70, 3369
24. Van Brabandt, W.; Van Landeghem, R.; De Kimpe, N. Org. Lett. 2006, 8, 1105
25. Van Brabandt, W.; Dejaegher, Y.; Van Landeghem, R.; De Kimpe, N. Org. Lett. 2006, 8, 1101
26. Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K.; Yamashita, M.; Abe, R. J. Org. Chem. 1991, 56, 5263
27. Alcaide, B.; Aly, M. F.; Sierra, M. A. Tetrahedron Lett. 1995, 36, 3401
28. Speeter, M. E.; Maroney, W. H. J. Am. Chem. Soc. 1954, 76, 5810
29. Sammes, P. G.; Smith, S. J. Chem. Soc., Chem. Commun. 1983, 682
30. D'hooghe, M.; Dekeukeleire, S.; De Kimpe, N. Org. Biomol. Chem. 2008, 6, 1190
31. D'hooghe, M.; Dekeukeleire, S.; Mollet, K.; Lategan, C.; Smith, P. J.; Chibale, K.; De Kimpe, N. J. Med. Chem. 2009, 52, 4058
32. D'hooghe, M.; Mollet, K.; Dekeukeleire, S.; De Kimpe, N. Org. Biomol. Chem. 2010, 8, 607
33. Bandini, E.; Favi, G.; Martelli, G.; Panunzio, M.; Piersanti, G. Org. Lett. 2000, 2, 1077
34. Van Driessche, B.; Van Brabandt, W.; D'hooghe, M.; Dejaegher, Y.; De Kimpe, N. Tetrahedron 2006, 62, 6882
35. Begley, M. J.; Crombie, L.; Haigh, D.; Jones, R. C. F.; Osborne, S.; Webster, R. A. B. J. Chem. Soc., Perkin Trans. 1 1993, 2027
36. Crombie, L.; Jones, R. C. F.; Osborne, S.; Mat-Zin, A. R. J. Chem. Soc., Chem. Commun. 1983, 959
37. Van Brabandt, W.; Vanwalleghem, M.; D'hooghe, M.; De Kimpe, N. J. Org. Chem. 2006, 71, 7083
38. Barrow, K. D.; Spotswood, T. M. Tetrahedron Lett. 1965, 6, 3325
39. Decazes, J.; Luche, J. L.; Kagan, H. B. Tetrahedron Lett. 1970, 11, 3361
40. Xu, J. Arkivoc 2009, ix) 21
41. Jiao, L.; Liang, Y.; Xu, J. X. J. Am. Chem. Soc. 2006, 128, 6060
42. McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568
43. Durrat, F.; Sanchez, M. V.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 19, 3286
44. Graham, A.; Wadsworth, A. H.; Thornton-Petta, M.; Rayner, C. M. Chem. Commun. 2001, 11, 966
45. Abbaspour Tehrani, K.; Van Syngel, K.; Boelens, M.; Contreras, J.; De Kimpe, N.; Knight, D. W. Tetrahedron Lett. 2000, 41, 2507
46. Martinez, A.; Elguero, J.; Mo, O.; Yanez, M. J. Mol. Struct. 1994, 115, 45
47. Kim, H. Y.; Talukdar, A.; Cushman, M. Org. Lett. 2006, 8, 1085
48. Lee, K.-D.; Suh, J.-M.; Park, J.-H.; Ha, H.-J.; Choi, H. G.; Park, C. S.; Chang, J. W.; Lee, W. K.; Dong, Y.; Yun, H. Tetrahedron 2001, 57, 8267