One-pot asymmetric synthesis of α-trifluoromethylated amines from α-trifluoromethyl ketones

Tetrahedron

Volumn 66, Issue 46, 2010, Pages 8933-8937

  Xu, Jian ^a   Liu, Zhen Jiang ^b   Yang, Xian Jin ^a,b   Wang, Li Min ^a,b   Chen, Guan Long ^a   Liu, Jin Tao ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Trifluoromethylated amine; Asymmetric synthesis; N tert Butanesulfinamide; Trifluoromethyl ketone

Indexed keywords

ALPHA TRIFLUOROMETHYL KETONE; ALPHA TRIFLUOROMETHYLATED AMINE DERIVATIVE; AMINE; KETONE; N (1,1,1 TRIFLUORO 5 PHENYLPENTAN 2 YL) TERT BUTANESULFINAMIDE; N (1,1,1 TRIFLUORODECAN 2 YL) TERT BUTANESULFINAMIDE; N (2,2,2 TRIFLUORO 1 (4 METHOXYPHENYL) ETHYL] TERT BUTANESULFINAMIDE; N (2,2,2 TRIFLUORO 1 4 TOLYLETHYL) TERT BUTANESULFINAMIDE; N (2,2,2 TRIFLUORO 1 PHENYLETHYL) TERT BUTANESULFINAMIDE; N [1 (4 BROMOPHENYL) 2,2,2 TRIFLUOROETHYL) TERT BUTANESULFINAMIDE; N [1 (4 BROMOPHENYL) 2,2,2 TRIFLUOROETHYL] TERT BUTANESULFINAMIDE; N [2,2,2 TRIFLUORO 1 (4 METHOXYPHENYL) ETHYL] TERT BUTANESULFINAMIDE; N TERT BUTANESULFINAMIDE; N TERT BUTANESULFINYL ALPHA TRIFLUOROMETHYL KETIMINE DERIVATIVE; SULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 77958190163     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.09.047     Document Type: Article

References (62)

1. I. Ojima, J.R. McCarthy, and J.T. Welch Biomedical Frontiers of Fluorine Chemistry ACS Symposium Series 639 1996 American Chemical Society Washington, DC
2. R. Filler, Y. Kobayashi, and Y.L. Yagulpolskii Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications 1993 Elsevier Amsterdam
3. R.E. Banks, B.E. Smart, and J.C. Tatlow Organofluorine Chemistry: Principles and Commercial Applications 1994 Plenum New York, NY
4. J.T. Welch, S. Eshwarakrishman, Fluorine in Bioorganic Chemistry 1991 Wiley New York, NY
5. T. Hiyama Organofluorine Compounds, Chemistry and Application 2000 Springer Berlin, Germany
6. K. Uneyama Organofluorine Chemistry 2006 Blackwell Oxford
7. For reviews, see:
8. J.-A. Ma, and D. Cahard Chem. Rev. 104 2004 6119
9. G.K.S. Prakash, and M. Mandal J. Fluorine Chem. 112 2001 123
10. T. Billard, and B.R. Langlois Eur. J. Org. Chem. 2007 891
11. G.A. Olah, G.K.S. Prakash, and M. Mandal Angew. Chem., Int. Ed. 40 2001 589
12. G.K.S. Prakash, M. Mandal, and G.A. Olah Org. Lett. 3 2001 2847
13. G.K.S. Prakash, and M. Mandal J. Am. Chem. Soc. 124 2002 6538
14. C. Estivill, J. Mendizabal, A. Virgili, E. Monteagudo, T. Flor, F. Sánchez-Ferrando, A. Alvarez-Larena, and J.F. Piniella Tetrahedron 65 2009 171
15. V.L. Truong, M.S. Ménard, and I. Dion Org. Lett. 9 2007 683
16. A. Ishii, K. Higashiyama, and K. Mikami Synlett 1997 1381
17. D. Enders, and K. Funabiki Org. Lett. 3 2001 1575
18. F. Gosselin, A. Roy, P.D. O'Shea, C.-Y. Chen, and R.P. Volante Org. Lett. 6 2004 641
19. W.H. Pirkle, and J.R. Hauske J. Org. Chem. 42 1977 2436
20. B. Török, and G.K.S. Prakash Adv. Synth. Catal. 345 2003 165
21. F. Gosselin, P.D. O'Shea, S. Roy, R.A. Reamer, C.-Y. Chen, and R.P. Volante Org. Lett. 7 2005 355
22. For other examples for the asymmetric synthesis of α- trifluoromethylated amines, see:
23. H. Kawai, A. Kusuda, S. Nakamura, M. Shiro, and N. Shibata Angew. Chem., Int. Ed. 48 2009 6324
24. Y. Wang, and H.S. Mosher Tetrahedron Lett. 32 1991 987
25. V.A. Soloshonok, and T. Ono J. Org. Chem. 62 1997 3030
26. A. Ishii, F. Miyamoto, K. Higashiyama, and K. Mikami Chem. Lett. 1998 119
27. J. Jiang, R.J. DeVita, G.A. Doss, M.T. Goulet, and M.J. Wyvratt J. Am. Chem. Soc. 121 1999 593
28. J. Jiang, H. Shah, and R.J. DeVita Org. Lett. 5 2003 4101
29. W. Xu, and W.R. Dolbier Jr. J. Org. Chem. 70 2005 4741
30. 3-substituted N-tert-butylsulfinyl imines, see:
31. see Ref. 5a;
32. H. Wang, X.-M. Zhao, Y.-H. Li, and L. Lu Org. Lett. 8 2006 1379
33. 3-substituted N-p-tolylsulfinyl imines, see:
34. A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J.G. Soler, S.V. Meille, W. Panzeri, F. Viani, A. Volonterio, and M. Zanda Eur. J. Org. Chem. 2001 1449
35. P. Bravo, M. Crucianelli, B. Vergani, and M. Zanda Tetrahedron Lett. 38 1998 7771
36. M. Crucianelli, F. De Angelis, F. Lazarro, L. Malpezzi, A. Volonterio, and M. Zanda J. Fluorine Chem. 125 2004 573
37. J.L.G. Ruano, T. Haro, R. Singh, and M.B. Cid J. Org. Chem. 73 2008 1150
38. X.-J. Wang, Y. Zhao, and J.-T. Liu Org. Lett. 9 2007 1343
39. Z.-J. Liu, Y.-Q. Mei, and J.-T. Liu Tetrahedron 63 2007 855
40. Y. Zhao, X.-J. Wang, and J.-T. Liu Synlett 2008 1017
41. X.-J. Wang, Y. Zhao, and J.-T. Liu Synthesis 2008 3967
42. F. Zhang, X.-J. Wang, C.-X. Cai, and J.-T. Liu Tetrahedron 65 2009 83
43. Z.-J. Liu, and J.-T. Liu Chem. Commun. 2008 5233
44. J. Tanuwidjaja, H.M. Peltier, and J.A. Ellman J. Org. Chem. 72 2007 626
45. G.D. Borg, A. Cogan, and J.A. Ellman Tetrahedron Lett. 40 1999 6709
46. 4 under reflux for 20-24 h.
47. For the stereoselectivity reversal in hydride reduction of N-tert-butanesulfinyl imines, see:
48. L.R. Reddy, S.G. Das, Y. Liu, and M. Prashad J. Org. Chem. 75 2010 2236
49. M. Martjuga, D. Shabashov, S. Belyakov, E. Liepinsh, and E. Suna J. Org. Chem. 75 2010 2357
50. J.T. Colyer, N.G. Anderson, J.S. Tedrow, T.S. Soukup, and M.M. Faul J. Org. Chem. 71 2006 6859
51. B. Denolf, E. Leemans, and N. De Kimpe J. Org. Chem. 72 2007 3211
52. G. Chelucci, S. Baldino, S. Chessa, G.A. Pinna, and F. Soccolini Tetrahedron: Asymmetry 17 2006 3163
53. T. Kochi, T.P. Tang, and J.A. Ellman J. Am. Chem. Soc. 124 2002 6518
54. T. Kochi, T.P. Tang, and J.A. Ellman J. Am. Chem. Soc. 125 2003 11276
55. T. Kochi, and J.A. Ellman J. Am. Chem. Soc. 126 2004 15652
56. H.M. Peltier, and J.A. Ellman J. Org. Chem. 70 2005 7342
57. 2O was still proved to be the best solvent considering both the diastereoselectivity and the yield of the reaction.
58. T. Kitazume, and T. Yamazaki Experimental Methods in Organic Fluorine Chemistry 1998 Kodansha Tokyo pp 9-10
59. see Ref. 1f, pp 81-89.
60. see Ref. 2a.
61. D. O'Hagan Chem. Soc. Rev. 37 2008 308
62. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320