Efficient synthesis of fluorinated α- And β-amino nitriles from fluoroalkylated α,β-unsaturated imines

Tetrahedron

Volumn 67, Issue 8, 2011, Pages 1575-1579

  Palacios, Francisco ^a   Ochoa De Retana, Ana M ^a   Pascual, Sergio ^a   Fernández De Trocóniz, Guillermo ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Amino acid derivatives; Fluorinated and amino nitriles; Fluorinated , unsaturated imines; Fluoroalkylated enamines; Phosphorylated enamines

Indexed keywords

ACETONITRILE; ALKYL GROUP; ALPHA AMINO ACID; BETA AMINO ACID; CYANIDE; FLUORINE DERIVATIVE; IMINE; NITRILE; TRIMETHYLSILYL DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; HYDROLYSIS; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 79551558383     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.046     Document Type: Article

References (82)

1. J.T. Welch, S. Eswarakrishnan, Fluorine in Bioorganic Chemistry 1991 Wiley New York, NY
2. I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology 2009 J. Wiley Chischester, UK
3. R.D. Chambers Fluorine in Organic Chemistry 2nd ed. 2004 Blackwell London
4. P. Kirsch Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim
5. V.A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets 1999 Wiley New York, NY
6. V.P. Kukhar, V.A. Soloshonok, Fluorine Containing Amino Acids, Synthesis and Properties 1995 Wiley New York, NY
7. For recent reviews see:
8. H.J. Federsel Acc. Chem. Res. 42 2009 671 680
9. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
10. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
11. K. Müller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
12. K.L. Kirk J. Fluorine Chem. 127 2006 1013 1029
13. For recent contributions see:
14. H.P. Chiu, B. Kokona, R. Fairman, and R.P. Cheng J. Am. Chem. Soc. 131 2009 13192 13343
15. M. Salwiczek, S. Samsonov, T. Vagt, E. Nyakutura, E. Fleige, J. Numata, H. Coelten, M.T. Pisabarro, and B. Koksch Chem. - Eur. J. 15 2009 7628 7636
16. H. Meng, and K. Kumar J. Am. Chem. Soc. 129 2007 15615 15622
17. B.C. Buer, R. de la Salud-Bea, H.M. Al Hashimi, E. Marsh, and G. Neil Biochemistry 48 2009 10810 10817
18. H. Meng, S.T. Krishnaji, M. Beinborn, and K. Kumar J. Med. Chem. 151 2008 7303 7307
19. C. Binkert, M. Frigerio, A. Jones, S. Meyer, C. Pesenti, L. Prade, F. Viani, and M. Zanda ChemBioChem 7 2006 181 186
20. For recent eviews see:
21. J. Streuff, D.E. White, S.C. Virgil, and B.M. Stoltz Nature Chem. 2 2010 192 196
22. A.M. Dumas, and E. Fillion Acc. Chem. Res. 43 2010 440 454
23. D.C. Koester, and D.B. Werz Angew. Chem., Int. Ed. 48 2009 7971 7973
24. N.K. Undavia, B.S. Patwa, H.D. Navadiya, A.R. Jivani, and P.N. Dave Int. J. Chem. Sci. 7 2009 1019 1026
25. For recent reviews see
26. M.X. Wang Chimia 63 2009 331 333
27. J.A. Gonzalez-Vera, M.T. Garcia-Lopez, and R. Herranz Mini-Rev. Org. Chem. 5 2008 209 221
28. A. Strecker Ann. Chem. Pharm. 75 1850 27 45
29. S.J. Connon Angew. Chem., Int. Ed. 47 2008 1176 1178
30. T. Vilaivan, W. Bhanthumunavin, and Y. Sritana-Anant Curr. Org. Chem. 9 2005 1315 1392
31. H. Gröger Chem. Rev. 103 2003 2795 2827
32. H. Wang, X. Zhao, Y. Li, and L. Lu Org. Lett. 8 2006 1379 1381
33. Y. Yamasaki, T. Maekawa, T. Ishihara, and T. Ando Chem. Lett. 1985 1387 1390
34. G.K.S. Prakash, T. Mathew, C. Panja, S. Alconcel, H. Vaghoo, C. Do, and G.A. Olah Proc. Natl. Acad. Sci. U.S.A. 104 2007 3703 3706
35. F. Huguenot, and T. Brigaud J. Org. Chem. 71 2006 7075 7078
36. G.K.S. Prakash, T.E. Thomas, I. Bychinskaya, A.G. Prakash, C.H. Panja, H. Vaghoo, and G.A. Olah Green Chem. 10 2008 1105 1110
37. For reviews of 1-azadienes see
38. B. Groenendal, E. Ruijer, and R.V.A. Orru Chem. Commun. 2008 5474 5489
39. S. Jayakumar, M.P.S. Ishar, and M.P. Mahajan Tetrahedron 58 2002 379 471
40. P. Buonora, J.C. Olsen, and T. Oh Tetrahedron 57 2001 6099 6138
41. For recent contributions see:
42. L. Singh, M.P.S. Ishar, M. Elango, V. Subramaniam, V. Gupta, and P. Kanwal J. Org. Chem. 73 2008 2224 2233
43. J.Y. Lu, and H.D. Arndt J. Org. Chem. 72 2007 4205 4212
44. J. Esquivias, R. Gomez Arrayas, and J.C. Carretero J. Am. Chem. Soc. 129 2007 1480 1481
45. For recent contributions see:
46. A. Mizuno, H. Kusama, and N. Iwasawa Angew. Chem., Int. Ed. 48 2009 8318 8320
47. Y. Lu, and B.A. Arndtsen Org. Lett. 11 2009 1369 1372
48. M. Atobe, N. Yamazaki, and C. Kibayashi Tetrahedron Lett. 46 2005 2669 2673
49. M.J. Schnermann, and D.L. Boger J. Am. Chem. Soc. 127 2005 15704 15705
50. Contributions to selective 1,2 addition to α,β-unsaturated imines:
51. B. Groenendaal, D.J. Vugts, R.F. Schmitz, F.J.J. de Kanter, E. Ruijer, M.B. Groen, and R.V.A. Orru J. Org. Chem. 73 2008 719 722
52. G.K.S. Prakash, M. Mandal, and G.A. Olah Org. Lett. 3 2001 2847 2850
53. S.E. Denmark, and C.M. Stiff J. Org. Chem. 65 2000 5875 5878
54. Recent contributions to selective conjugate addition to α,β-unsaturated imines:
55. J. Vicario, D. Aparicio, and F. Palacios J. Org. Chem. 74 2009 452 455
56. F. Palacios, and J. Vicario Org. Lett. 8 2006 5405 5408
57. M. Shimizu, A. Takahashi, and S. Kawai Org. Lett. 8 2006 3585 3587
58. Contributions to double addition to α,β-unsaturated imines:
59. E. Van Meenen, K. Moonen, A. Verwée, and C.V. Stevens J. Org. Chem. 71 2006 7903 7906
60. K. Moonen, E. Van Meenen, A. Verwée, and C.V. Stevens Angew. Chem., Int. Ed. 44 2005 7407 7411
61. M. Shimizu, M. Kamiya, and I. Hachiya Chem. Lett. 34 2005 1456 1457
62. W.H. Pearson, and V.A. Jacobs Tetrahedron Lett. 35 1994 7001 7004
63. M. Teng, and F.W. Fowler J. Org. Chem. 55 1990 5646 5653
64. W.T. Brady, and C.H. Shieh J. Org. Chem. 48 1983 2499 2502
65. For reviews see:
66. F. Palacios, D. Aparicio, G. Rubiales, C. Alonso, and J.M. de los Santos Curr. Org. Chem. 13 2009 810 828
67. F. Palacios, D. Aparicio, G. Rubiales, C. Alonso, and J.M. de los Santos Tetrahedron 63 2006 523 575
68. For contributions of creation of the CN bouble bond by means of this process see:
69. F. Palacios, E. Herrán, G. Rubiales, and C. Alonso Tetrahedron 63 2007 5669 5676
70. F. Palacios, E. Herrán, C. Alonso, G. Rubiales, B. Lecea, M. Ayerbe, and F.P. Cossío J. Org. Chem. 71 2006 6020 6030
71. F.P. Cossío, C. Alonso, B. Lecea, M. Ayerbe, G. Rubiales, and F. Palacios J. Org. Chem. 71 2006 2839 2847
72. F. Palacios, C. Alonso, G. Rubiales, and M. Villegas Tetrahedron 61 2005 2779 2794
73. F. Palacios, J. Vicario, and D. Aparicio J. Org. Chem. 71 2006 7690 7696
74. F. Palacios, J. Vicario, and A. Maliszewska J. Org. Chem. 72 2007 2682 2685
75. F. Palacios, A.M. Ochoa de Retana, S. Pascual, and J. Oyarzabal Org. Lett. 4 2002 769 772
76. F. Palacios, D. Aparicio, and J. Vicario Eur. J. Org. Chem. 2002 4131 4136
77. F. Palacios, D. Aparicio, J. García, E. Rodríguez, and A. Fernández-Acebes Tetrahedron 57 2001 3131 3141
78. F. Palacios, A.M. Ochoa de Retana, and J.M. Alonso J. Org. Chem. 71 2006 6141 6148
79. F. Palacios, A.M. Ochoa de Retana, J. Oyarzabal, S. Pascual, and G. Fernandez de Troconiz J. Org. Chem. 73 2008 4568 4574
80. F. Palacios, A.M. Ochoa de Retana, S. Pascual, and J. Oyarzabal J. Org. Chem. 69 2004 8767 8774
81. For a review of β-aminophosphonates see: F. Palacios, C. Alonso, and J.M. de los Santos Chem. Rev. 105 2005 899 931
82. 26