Preparation of fluoroalkyl imines, amines, enamines, ketones, α-amino carbonyls, and α-amino acids from primary enamine phosphonates

Journal of Organic Chemistry

Volumn 69, Issue 25, 2004, Pages 8767-8774

  Palacios, Francisco ^a   Ochoa De Retana, Ana María ^a   Pascual, Sergio ^a   Oyarzabal, Julen ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMINO ACIDS; CHEMICAL BONDS; HYDROLYSIS; KETONES; OLEFINS;

ACID HYDROLYSIS; ALKYLPHOSPHONATES;

AMINES;

ALDEHYDE; ALPHA AMINO ACID; AMINE; CARBON; CARBONYL DERIVATIVE; ENAMINE; ENAMINE PHOSPHONATE; IMINE; KETONE DERIVATIVE; NITRILE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; HYDROLYSIS; OLEFINATION; OXIDATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

ACETALDEHYDE; AMINES; AMINO ACIDS; IMINES; KETONES; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 10044261122     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048682m     Document Type: Article

References (98)

1. (a) Fluorine in Bioorganic Chemistry; Welch, J. T., Eswarakrishnan, S., Eds.; Wiley: New York, 1991.
2. (b) Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; American Chemical Society: Washington D.C., 1991.
3. (a) Chambers, R. D. Fluorine In Organic Chemistry, 2nd ed.; Blackwell: London, 2004
4. (b) Organofluorine Compounds: Chemistry and Applications; Hiyama, T., Ed.; Springer: Berlin, 2000.
5. (c) Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions; Ramachandran, P. V., Ed.; American Chemical Society: Washington D.C., 1999.
6. (a) Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; Wiley: New York, 1999.
7. (b) Fluorine-Containing Amino Acids: Synthesis and Applications; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: New York, 1995.
8. (c) Banks, R. E.; Smarts, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum: New York, 1994.
9. For an excellent review, see: Rappoport, Z. In The Chemistry of Enamines. The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1994.
10. For recent reviews, see: (a) Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433.
11. (b) Duthaler, R. O. Angew. Chem., Int. Ed. 2003, 42, 975.
12. (c) Elassar, A. Z. A.; El-Khair, A. A: Tetrahedron 2003, 59, 8463.
13. For reviews, see: (a) Shatzmiller, S.; Lidor, R. in ref 1, Part 2, 1994; p 1507.
14. (b) Martin S. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 475.
15. (a) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273.
16. (b) Stork, G. Med. Res. Rev. 1999, 19, 370.
17. (c) Cuvigny, T.; Normant, H. Synthesis 1977, 198.
18. (d) Stork, G.; Brizzolarra, A.; Landesman, H.; Szmuszkovicz, J.; Terrele, R. J. Am. Chem. Soc. 1963, 85, 207.
19. (a) Palacios, F.; Aparicio, D.; García, J.; Rodríguez, E.; Fernández, A. Tetrahedron 2001, 56, 3131.
20. (b) Palacios, F.; Aparicio, D.; García, J.; Vicario, J.; Ezpeleta, J. M. Eur. J. Org. Chem. 2001, 3357.
21. (c) Palacios, F.; Aparicio, D.; García, J.; Rodríguez, E. Eur. J. Org. Chem. 1998, 1413, 3.
22. (d) Palacios, F.; Aparicio, D.; García, J. Tetrahedron 1996, 52, 9609.
23. (a) Novak, B. M.; Cafmayer, J. J. Am. Chem. Soc. 2001, 123, 11083.
24. (b) Erker, G.; Riedel, M.; Koch, S.; Jöedicke, T.; Wüerthwein, E. U. J. Org. Chem. 1995, 60, 5284.
25. (a) Palacios, F.; Aparicio, D.; Ochoa de Retana, A. M.; de los Santos, J. M.; Gil, J. I.; Lopez de Munain, R. J. Org. Chem. 2002, 67, 7283.
26. (b) Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; Ezpeleta, J. M. J. Org. Chem. 2000, 65, 3213.
27. (a) Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; Alonso, J. M. Tetrahedron: Asymmetry 2002, 13, 2541.
28. (b) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1999, 55, 13767.
29. (c) Palacios, F.; Pagalday, J.; Piquet, V.; Dahan, F.; Baceiredo, A.; Bertrand, G. J. Org. Chem. 1997, 62, 292.
30. (a) Palacios, F.; Herran, E.; Rubiales, G.; Ezpeleta, J. M. J. Org. Chem. 2002, 67, 2131.
31. (b) Palacios, F.; Ochoa de Retana, A. M.; Gil, J. I.; Lopez de Munain, R. Org. Lett. 2002, 4, 2415.
32. (c) Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron 1999, 55, 5947.
33. (a) Palacios, F.; Oyarzabal, J.; Ochoa de Retana, A. M. Tetrahedron Lett. 1996, 37, 4577.
34. (b) Barluenga, J.; Lopez, F.; Palacios, F.; Cano, F. H.; Foces, M. C. J. Chem Soc, Perkin Trans, 1 1988, 2329.
35. (a) López, F.; Peláez, E.; Palacios, F.; Barluenga, J.; García, J.; Tejerina, B.; García, A. J. Org. Chem. 1994, 59, 1984.
36. (a) Palacios, F.; Ochoa de Retana, A. M.; Pascual, S.; Lopez de Munain, R. Tetrahedron Lett. 2002, 43, 5917.
37. (b) Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron 1999, 55, 3091.
38. (c) Barluenga, J.; López, F.; Palacios, F. Tetrahedron Lett. 1987, 28, 2875.
39. Johnson, A. W.; Kaska, W. C.; Starzewski, K. A. O.; Dixon, D. A. Ylides and Imines of Phosphorus; John Wiley & Sons: New York, 1993; pp 307-358.
40. (a) Toy, A. D. F.; Walsh, E. N. Phosphorus Chemistry in Everyday Living; American Chemical Society: Washington D.C., 1987.
41. (b) Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992.
42. (a) Hojo, M.; Masuda, M.; Okada, E. Tetrahedron Lett. 1989, 45, 6173.
43. (b) Wanner, M. J.; Hageman, J. M.; Koomen, G. J.; Pandit, U.K. J. Med. Chem. 1980, 23, 85.
44. (c) Krespan, C. G. J. Org. Chem. 1969, 34, 42.
45. (b) Doussot, P.; Portella, Ch. J. Org. Chem. 1993, 58, 6675.
46. (a) Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Neille, S. V.; Zanda, M.; Cavicchio, G.; Crucianelli, M. J. Org. Chem. 1996, 61, 3375.
47. (b) Bouillon, J. P.; Maliverny, C.; Janusek, Z.; Viehe, H. G. Bull. Soc. Chim. Fr. 1997, 134, 47.
48. (c) Lee, L. F.; Howe, R. K. J. Org. Chem. 1984, 49, 4780.
49. (d) Cen, W.; Ni, Y.; Shen, Y. J. Fluorine Chem. 1995, 73, 161.
50. (e) Fustero, S.; Fiera, J.; Sanz-Cervera, J. F.; Catalan, S.; Ramirez de Arellano, C. Org. Lett 2004, 6, 1417.
51. (f) Luo, B. H.; Guan, H. P.; Hu, C. M. Synlett 1997, 1261.
52. (g) Lee, L. F.; Sing, Y. L. J. Org. Chem. 1990, 55, 380.
53. (h) Von Allwönden, U.; Röschenthaler, G. V. Chem. Zeitg. 1988, 112, 69.
54. For a preliminary communication, see: Palacios, F.; Pascual, S.; Oyarzabal, J.; Ochoa de Retana, A. M Org. Lett. 2002, 4, 769.
55. 2): Reisner, D. B.; Horning, E. C. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, pp 144-145.
56. 2CN are liquid and were added to the solution of phosphonates 2 in the presence of LDA.
57. (a) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
58. (b) Duncan, M.; Gallager, M. J. Org. Magn. Reson. 1981, 15, 37.
59. (a) For a review see: Nenajdenko, V. G.; Sanin, A. V.; Balenkova, E. S. Russ. Chem. Rev. 1999, 68, 437.
60. For recent contributions, see: (b) Peng, W.; Zhu, S. Tetrahedron 2003, 59, 4641.
61. (c) Andrew, R. J.; Mellor, J. M. Tetrahedron 2000, 56, 7267.
62. (d) Funabiki, K.; Nakamura, H.; Matsui, M.; Shibata, K. Synlett 1999, 756.
63. For recent contributions, see: (a) Yoshimatsu, M.; Hibino, M. Chem. Pharm. Bull. 2000, 48, 1395.
64. (b) Bishop, L. P.; Magss, J. L.; O'Neill, P. M.; Park, B. K. J. Pharm. Exp. Ther 1999, 289, 511.
65. (c) Boger, D. L.; Sato, H.; Lerner, A. E.; Austin, B. J.; Patterson, J. E.; Patricelli, M. P.; Cravatt, B. F. Bioorg. Med. Chem. Lett. 1999, 9, 265.
66. (d) Kawase, M.; Harada, H.; Saito, C.; Cui, J. M.; Tani, S. Bioorg. Med. Chem. Lett. 1999, 9, 193.
67. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
68. (b) Singh, R. P.; Ca, G. F.; Kichmeier, R. L.; Sheeve, J. M. J. Org. Chem. 1999, 64, 483.
69. (c) Wiedemann, W.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 820.
70. (d) Andrew, R. J.; Mellor, J. M. Tetrahedron 2000, 56, 7261.
71. (e) Sanin, A. V.; Nenajdenko, V. G.; Smolko, K.; Denisenko, D. I.; Balenkova, E. S. Synthesis 1999, 842.
72. (f) Huang, W. S.; Yuan, C. Y. J. Chem. Soc., Perkin Trans. 1 1995, 741.
73. (g) Mo, X. S.; Huang, Y. Z. Synlett 1995, 180.
74. (h) Xu, Y.; Dolbier, W. R. Tetrahedron Lett. 1998, 39, 9151.
75. (i) Linderman, R. J.; Jamois, E. A.; Tennyson, S. D. J. Org. Chem. 1995, 59, 957.
76. (j) Hata, H.; Kobayashi, T.; Amii, H.; Uneyama, K.; Welch, J. T. Tetrahedron Lett. 2002, 43, 6099.
77. (a) Yamasaki, Y.; Maekawa, T.; Ishihara, T.; Ando, T. Park, B. K. Chem. Lett. 1985, 1387.
78. (b) Ishihara, T.; Maekawa, T.; Ando, T. Park, B. K. Tetrahedron Lett. 1983, 24, 1387.
79. (c) Huang, W. S.; Yuan, C. Y. J. Chem. Soc., Perkin Trans. 1 1995, 741.
80. (d) Mae, M.; Matsuura, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2002, 43, 2069.
81. For an example of selective 1,2- and 1,4-addition of organolithium reagents to unsaturated aldimines, see: Tomioka, K.; Shioya, Y.; Nagaoka, Y.; Yamada, K. J. Org. Chem. 2001, 66, 7051 and references cited therein.
82. (a) Ohba, T.; Ikeda, E.; Wakayama, J.; Takei, H. Bioorg. Med. Chem. Lett. 1996, 6, 219.
83. (b) Palfreyman, M. G.; McDonald, I. A.; Bey, P.; Danzin, C.; Zreika, M.; Cremer, G. J. Neural. Transm., Suppl. 1994, 41, 407.
84. (c) Bey, P.; Fozard, J.; Lacoste, J. M.; McDonald, I. A.; Zreika, M.; Palfreyman, M. G. J. Am. Chem. Soc. 1984, 27, 9.
85. (a) Xu, Y.; Dolbier, W. R. J. Org. Chem. 2000, 65, 2134.
86. (b) Weygand, F.; Steglich, W.; Oettmeir, W.; Maierhofer, A.; Loy, R. S. Angew. Chem., Int. Ed. Engl. 1966, 5, 600.
87. (c) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett, 2001, 77.
88. (d) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847.
89. The oxidation of the α-amino aldehyde to the corresponding α-amino acid takes place very easily in the presence of air.
90. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
91. (b) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. J. Org. Chem. 2002, 67, 1941.
92. (a) Fustero, S.; Navarro, A.; Pina, B.; Soler, J. G.; Bartolome, A.; Asensio, A.; Simón, A.; Bravo, P.; Fronza, G.; Volonteiro, A,; Zanda, M. Org. Lett. 2001, 3, 2621.
93. (b) Davis, F. A.; Srirajan, V.; Titus, D. D. J. Org. Chem. 1999, 64, 6931.
94. (a) Bravo, P.; Crucianelli, M.; Fronza, G.; Zanda, M. Synlett 1996, 249.
95. (b) Bravo, P.; Crucianelli, M.; Farina, A.; Valdo Meille, S.; Volonterio, A.; Zanda, M. Eur. J. Org. Chem. 1998, 435.
96. (c) Abouabdellah A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005.
97. (d) Van Hijfte, L.; Heydt, V.; Kolb, M. Tetrahedron Lett. 1993, 34, 4793.
98. Panzeri, A.; Nesi, M.; Di Salle, E. PCT Int. Appl. WO 9403476, 1994; Chem. Abstr. 1994, 121, 134563.