Highly diastereoselective synthesis of enantiopure β-trifluoromethyl β-amino alcohols from chiral trifluoromethyl oxazolidines (Fox)

Organic Letters

Volumn 14, Issue 2, 2012, Pages 604-607

  Simon, Julien ^a   Chelain, Evelyne ^a   Brigaud, Thierry ^a  

^a Université Paris Seine   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; FLUORINE DERIVATIVE; IMINE; OXAZOLE DERIVATIVE; OXAZOLIDINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; STEREOISOMERISM; SYNTHESIS;

AMINO ALCOHOLS; FLUORINE COMPOUNDS; IMINES; METHYLATION; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 84856116733     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2032174     Document Type: Article

References (49)

1. Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576
2. Klingler, F. D. Acc. Chem. Res. 2007, 40, 1367-1376
3. Lee, H.-S.; Kang, S. H. Synlett 2004, 1673-1685
4. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159-2231
5. Senanayake, C. H. Aldrichimica Acta 1998, 31, 3-15
6. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875
7. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151-4202
8. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45
9. Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467-3494
10. de Parrodi, C. A; Juaristi, E. Synlett 2006, 2699-2715
11. Vicario, J. L.; Badia, D.; Carrillo, L.; Reyes, E.; Etxebarria, J. Curr. Org. Chem. 2005, 9, 219-235
12. Bioorganic and Medicinal Chemistry of Fluorine; Begue, J.-P.; Bonnet-Delpon, D., Eds.; Wiley: Hoboken, NJ, 2008.
13. Fluorine In Medicinal Chemistry And Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: 2009.
14. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Kirsch, P., Ed.; Wiley-VCH: Weinheim, 2004.
15. Organofluorine chemistry; Uneyama, K., Ed.; Blackwell Publishing: Oxford, 2006.
16. Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; American Chemical Society: Washington, DC, 2005.
17. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975-996
18. Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119-6146
19. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43
20. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455-529
21. Bravo, P.; Crucianelli, M.; Ono, T.; Zanda, M. J. Fluorine Chem. 1999, 97, 27-49
22. Kuznetsova, L. V.; Pepe, A.; Ungureanu, I. M.; Pera, P.; Bernacki, R. J.; Ojima, I. J. Fluorine Chem. 2008, 129, 817-828
23. Binkert, C.; Frigerio, M.; Jones, A.; Meyer, S.; Pesenti, C.; Prade, L.; Viani, F.; Zanda, M. ChemBioChem 2006, 7, 181-186
24. Pesenti, C.; Arnone, A.; Bellosta, S.; Bravo, P.; Canavesi, M.; Corradi, E.; Frigerio, M.; Meille, S. V.; Monetti, M.; Panzeri, W.; Viani, F.; Venturini, R.; Zanda, M. Tetrahedron 2001, 57, 6511-6522
25. Molteni, M.; Pesenti, C.; Sani, M.; Volonterio, A.; Zanda, M. J. Fluorine Chem. 2004, 125, 1735-1743
26. Philippe, C.; Milcent, T.; Nguyen, T. N. T.; Crousse, B.; Bonnet-Delpon, D. Eur. J. Org. Chem. 2009, 30, 5215-5223
27. Marti, R. E.; Heinzer, J.; Seebach, D. Liebigs Annalen 1995, 1193-215
28. Sakai, T.; Yan, F.; Kashino, S.; Uneyama, K. Tetrahedron 1996, 52, 233-244
29. Uneyama, K.; Hao, J.; Amii, H. Tetrahedron Lett. 1998, 39, 4079-4082
30. Abouabdellah, A.; Begue, J.-P.; Bonnet-Delpon, D.; Nga, T. T. T. J. Org. Chem. 1997, 62, 8826-8833
31. Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S. V.; Zanda, M.; Cavicchio, G.; Crucianelli, M. J. Org. Chem. 1996, 61, 3375-3387
32. Volonterio, A.; Bravo, P.; Stefano, S. C.; Meille, S. V.; Zanda, M. Tetrahedron Lett. 1997, 38, 1847-1850
33. Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky, A. E.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424-3425
34. Volonterio, A.; Vergani, B.; Crucianelli, M.; Zanda, M.; Bravo, P. J. Org. Chem. 1998, 63, 7236-7243
35. Bravo, P.; Guidetti, M.; Viani, F.; Zanda, M.; Markovsky, A. L.; Sorochinsky, A. E.; Soloshonok, I. V.; Soloshonok, V. A. Tetrahedron 1998, 54, 12789-12806
36. Pesenti, C.; Arnone, A.; Aubertin, A. M.; Bravo, P.; Frigerio, M.; Panzeri, W.; Schmidt, S.; Viani, F.; Zanda, M. Tetrahedron Lett. 2000, 41, 7239-7243
37. Pytkowicz, J.; Stephany, O.; Marinkovic, S.; Inagaki, S.; Brigaud, T. Org. Biomol. Chem. 2010, 8, 4540-4542
38. Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 7075-7078
39. Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126
40. Grellepois, F.; Nonnenmacher, J.; Lachaud, F.; Portella, C. Org. Biomol. Chem 2011, 9, 1160-1168
41. Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382
42. Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Tetrahedron Lett. 1998, 39, 1199-1202
43. Gosselin, F.; Roy, A.; O'Shea, P. D.; Chen, C.-y.; Volante, R. P. Org. Lett. 2004, 6, 641-644
44. Black, W. C.; Bayly, C. I.; Davis, D. E.; Desmarais, S.; Falgueyret, J.-P.; Leger, S.; Li, C. S.; Masse, F.; McKay, D. J.; Palmer, J. T.; Percival, M. D.; Robichaud, J.; Tsoub, N.; Zambonia, R. Bioorg. Med. Chem. Lett. 2005, 154741-4744
45. Legros, J.; Meyer, F.; Coliboeuf, M.; Crousse, B.; Bonnet-Delpon, D.; Begue, J.-P. J. Org. Chem. 2003, 68, 6444-6446
46. Harper, S.; Ferrara, M.; Crescenzi, B.; Pompei, M.; Palumbi, M. C.; Di Muzio, J. M.; Donghi, M.; Fiore, F.; Koch, U.; Liverton, N. J.; Pesci, S.; Petrocchi, A.; Rowley, M.; Summa, V.; Gardelli, C. J. Med. Chem. 2009, 52, 4820-4837
47. Simon, J.; Nguyen, T. T.; Chelain, E.; Lensen, N.; Pytkowicz, J.; Chaume, G.; Brigaud, T. Tetrahedron: Asymmetry 2011, 22, 309-314
48. Fukuda, T.; Takehara, A.; Haniu, N.; Iwao, M. Tetrahedron: Asymmetry 2000, 11, 4083-4091
49. Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406-2410