Synthesis of γ-fluoro-α-amino acids by Claisen rearrangement

Journal of Fluorine Chemistry

Volumn 126, Issue 4, 2005, Pages 555-567

  Tranel, Frank ^a   Fröhlich, Roland ^a   Haufe, Günter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Amino acid fluoroallylesters; Ester enolate Claisen rearrangement; Fluorinated amino acids; Stereochemistry; Vinyl fluorides

Indexed keywords

EID: 23244452796     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.12.009     Document Type: Article

References (94)

1. R.M. Williams, J.E. Baldwin, and P.D. Magnus Synthesis of Optically Active Amiono Acids Organic Chemistry Series vol. 7 1989 Pergamon Press Oxford
2. R.O. Duthaler Tetrahedron 50 1994 1539 1650
3. A.S. Bommarius, M. Schwarm, K. Stingl, M. Kottenhahn, K. Huthmacher, and K. Drauz Tetrahedron: Asymm. 6 1995 2851 2888
4. K.-H. Park, and M.J. Kurth Tetrahedron 58 2002 8629 8659
5. T. Hohsaka, and M. Sisido Curr. Opin. Chem. Biol. 6 2002 809 815
6. J.T. Welch Tetrahedron 43 1987 3123 3197
7. V.P. Kukhar, V.A. Soloshonok, and Y.L. Yagupolskii Russ. Chem. Rev. 59 1990 89 102
8. V.P. Kukhar, and V.A. Soloshonok Russ. Chem. Rev. 60 1991 850 864
9. V.P. Kukhar, Y.T. Yagupolskii, I.I. Gerus, and M.T. Kolycheva Russ. Chem. Rev. 60 1991 1050 1058
10. I. Ojima J.R. McCarthy J.T. Welch Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 1996 American Chemical Society Washington
11. V.P. Kukhar J. Fluorine Chem. 69 1994 199 205
12. V.P. Kukhar V.A. Soloshonok Fluorine-Containing Amino Acids 1995 Wiley New York
13. V. Tolman Amino Acids 11 1996 15 36
14. G. Haufe, and S. Kröger Amino Acids 11 1996 409 424
15. A. Sutherland, and C.L. Willis Nat. Prod. Rep. 17 2000 621 631
16. X.-L. Qui, W.-D. Meng, and F.-L. Qing Tetrahedron 60 2004 6711 6745
17. B. Imperiali, and Synthetic Fluoropeptides as Pharmacologically Useful Compounds Synthetic Peptides in Biotechnology 1988 A.R. Liss Inc. pp. 97-129
18. R.V. Hoffman, and J. Tao Tetrahedron Lett. 39 1998 4195 4198
19. J. Qiu, and R.B. Silverman J. Med. Chem. 43 2000 706 720
20. F. Weygand, W. Steglich, W. Oettmeier, A. Meierhofer, and P.S. Loy Angew. Chem. 78 1966 640
21. F. Weygand, W. Steglich, and W. Oettmeier Chem. Ber. 103 1970 818 826
22. G. Höfle, and W. Steglich Chem. Ber. 104 1971 1408 1419
23. K. Burger, D. Hübl, and P. Geritschke J. Fluorine Chem. 27 1984 327 332
24. G. Bold, T. Allmendinger, P. Herold, L. Moesch, H.-P. Schär, and R.O. Duthaler Helv. Chim. Acta 75 1992 865 882
25. A. Arnone, D. Gestmann, S.V. Meille, G. Resnati, and G. Sidoti Chem. Commun. 1996 2569 2570
26. Y. Kokuryo, T. Nakatani, K. Kobayashi, Y. Tannura, K. Kawada, and M. Ohtani Tetrahedron: Asymm. 7 1996 3545 3551
27. A. Arnone, F. Blasco, and G. Resnati Tetrahedron 53 1997 17513 17518
28. R.J. Cregge, T.T. Curran, and W.A. Metz J. Fluorine Chem. 88 1998 71 77
29. P. Wipf, T.C. Henninger, and S.J. Geib J. Org. Chem. 63 1998 6088 6089
30. S. Marcotte, X. Pannecoucke, C. Feason, and J.-C. Quirion J. Org. Chem. 64 1999 8461 8464
31. F.A. Davis, V. Srirajam, and D.D. Titus J. Org. Chem. 64 1999 6931 6934
32. Y. Kokuryo, T. Nakatani, M. Kakinuma, M. Kabaki, K. Kawata, A. Kugimiya, K. Kawada, M. Matsumoto, R. Suzuki, and M. Ohtani Eur. J. Med. Chem. 35 2000 529 534
33. S. Kröger, and G. Haufe Amino Acids 12 1997 363 372
34. S. Kröger, and G. Haufe Liebigs Ann. Chem. 1997 1201 1206
35. G. Haufe, K.W. Laue, M.U. Triller, Y. Takeuchi, and N. Shibata Tetrahedron 54 1998 5929 5938
36. K.W. Laue, and G. Haufe Synthesis 1998 1453 1456
37. K.W. Laue, C. Mück-Lichtenfeld, and G. Haufe Tetrahedron 55 1999 10413 10424
38. K.W. Laue, S. Kröger, E. Wegelius, and G. Haufe Eur. J. Org. Chem. 2000 3737 3743
39. A.M. Martin Castro Chem. Rev. 104 2004 2939 3002
40. P.A. Bartlett, D.J. Tanzella, and J.F. Barstow Tetrahedron Lett. 23 1982 619 622
41. P.A. Bartlett, and J.F. Barstow J. Org. Chem. 47 1982 3933 3941
42. K. Katagiri, K. Tori, Y. Rimura, T. Yoshida, T. Nagasaki, and H. Minato J. Med. Chem. 10 1967 1149 1155
43. U. Cramer, A.G. Rehfeldt, and F. Spener Biochemistry 19 1980 3074 3080
44. M. Johnson, R. Raines, M. Chang, N. Esaki, K. Soda, and C. Walsh Biochemistry 20 1981 4325 4333
45. S. Tsubotani, Y. Funabashi, M. Takamoto, S. Hakoda, and S. Harada Tetrahedron 47 1991 8079 8090
46. N. Kurokawa, and Y. Ohfune J. Am. Chem. Soc. 108 1986 6041 6043
47. H. Baumann, and R.O. Duthaler Helv. Chim. Acta 71 1988 1025 1034
48. Q.B. Broxterman, B. Kaptein, J. Kamphuis, and H.E. Shoemaker J. Org. Chem. 57 1992 6286 6294
49. U. Kazmaier Angew. Chem. 106 1994 1046 1047
50. U. Kazmaier Angew. Chem., Int. Ed. Engl. 33 1994 998 999
51. U. Kazmaier J. Org. Chem. 59 1994 6667 6670
52. U. Kazmaier, and C. Schneider Synlett 1996 975 977
53. U. Kazmaier, and C. Schneider Synthesis 1998 1321 1326
54. U. Kazmaier Tetrahedron 50 1994 12895 12902
55. U. Kazmaier Synlett 1995 1138 1140
56. U. Kazmaier, and S. Maier J. Chem. Soc., Chem. Commun. 1995 1991 1992
57. U. Kazmaier, and C.H. Görbitz Synthesis 1996 1489 1493
58. U. Kazmaier, and S. Maier Tetrahedron 52 1996 941 954
59. U. Kazmaier J. Org. Chem. 61 1996 3694 3699
60. U. Kazmaier Tetrahedron Lett. 37 1996 5351 5354
61. U. Kazmaier Liebigs Ann./Recueil 1997 285 295
62. F.L. Zumpe, and U. Kazmaier Synlett 1998 434 436
63. U. Kazmaier, S. Maier, and F.L. Zumpe Synlett 2000 1523 1535
64. H. Mues, and U. Kazmaier Synthesis 2001 487 498
65. U. Kazmaier, and S. Maier J. Org. Chem. 64 1999 4574 4575
66. S. Maier, and U. Kazmaier Eur. J. Org. Chem. 2000 1241 1251
67. U. Kazmaier, and C. Schneider Tetrahedron Lett. 39 1998 817 818
68. C. Schneider, and U. Kazmaier Eur. J. Org. Chem. 1998 1155 1159
69. U. Kazmaier, and A. Krebs Tetrahedron Lett. 40 1999 479 482
70. U. Kazmeier, and A. Krebs Angew. Chem. 107 1995 2213 2214
71. U. Kazmeier, and A. Krebs Angew. Chem. Int. Ed. Engl. 34 1995 2012 2013
72. A. Krebs, and U. Kazmaier Tetrahedron Lett. 37 1996 7945 7946
73. J.M. Percy, and M.E. Prime J. Org. Chem. 63 1998 8049 8051
74. T. Konno, T. Daitoh, T. Ishihara, and H. Yamanaka Tetrahedron: Asymm. 12 2001 2743 2748
75. M. Schlosser, D. Michel, and S.L. Croft Synthesis 1996 591 593
76. T. Allmendinger, C. Angst, and H. Karfunkel J. Fluorine Chem. 72 1995 247 253
77. F. Tranel, and G. Haufe J. Fluorine Chem. 125 2004 1593 1608
78. J.F. Normant, O. Reboul, R. Sauvetre, H. Deshayes, D. Masure, and J. Villieras Bull. Soc. Chem. Fr. 1974 2072 2078
79. S.J. Brown, S. Corr, and J.M. Percy Tetrahedron Lett. 41 2000 5269 5273
80. J.H. Hong, K. Lee, Y. Choi, and C.K. Chu Tetrahedron Lett. 39 1998 3443 3446
81. K. Lee, Y. Choi, J.H. Hong, R.F. Schinazi, and C.K. Chu Nucleosides Nucleotides 18 1999 537 540
82. G. Gumina, Y. Chong, Y. Choi, and C.K. Chu Org. Lett. 2 2000 1229 1231
83. T. Ernet, and G. Haufe Synthesis 1997 953 956
84. O. Keller, W.E. Keller, G. van Look, and G. Wersin Org. Synth. 63 1985 160 170
85. F. Weygand, and R. Geiger Chem. Ber. 89 1956 647 656
86. B. Neises, and W. Steglich Angew. Chem. 90 1978 556 557
87. B. Neises, and W. Steglich Angew. Chem. Int. Ed. Engl. 17 1978 522 523
88. A. Hassner, and V. Alexanian Tetrahedron Lett. 1978 4475 4478
89. F. Weygand, W. Steglich, D. Mayer, and W.V. Phillipsborn Chem. Ber. 97 1964 2023 2028
90. Y. Masui, N. Chino, and S. Sakakibara Bull. Chem. Soc. Jpn. 53 1980 464 468
91. U. Kazmaier, Personal communication, September 2000.
92. S.J. Brown, S. Corr, and J.M. Percy Tetrahedron Lett. 41 2000 5269 5273
93. B.L. Lucht, and D.B. Collum Acc. Chem. Res. 32 1999 1035 1042
94. M. Imazawa, and F. Eckstein J. Org. Chem. 44 1979 2039 2041