Selective defluorination approach to N-Cbz-3,3-difluoro-2- difluoromethylenepyrrolidine and its application to 3,3-difluoroproline dipeptide synthesis

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8523-8526

  Guo, Yong ^a   Fujiwara, Kana ^a   Amii, Hideki ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOESTERS; DEFLUORINATION;

ESTERS; FLUORINATION; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL);

PEPTIDES;

3,3 DIFLUORO 2 DIFLUOROMETHYLENEPYRROLIDINE; 3,3 DIFLUOROPROLINE DERIVATIVE; AMINOESTER DERIVATIVE; DIPEPTIDE DERIVATIVE; ENAMINE; ESTER DERIVATIVE; IMINE; MAGNESIUM; METHYL GROUP; N (4 METHOXYPHENYL)BIS(TRIFLUOROMETHYL)IMINE; PERFLUOROENAMINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEFLUORINATION; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

DIPEPTIDES; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; PROLINE; PYRROLIDINES; STEREOISOMERISM;

EID: 35548952756     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070719q     Document Type: Article

References (157)

1. (a) Babu, I. R.; Hamill, E. K.; Kumar, K. J. Org. Chem. 2004, 69, 5468-5470.
2. (b) Wang, P.; Tang, Y.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 6900-6906.
3. (a) Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Kodansha, Ltd.: Tokyo, Japan, 1982.
4. (b) Ishikawa, N., Ed. Synthesis and Speciality of Organofluorine Compounds; CMC: Tokyo, Japan, 1987.
5. (c) Ishikawa, N., Ed. Biologically Active Organofluorine Compounds; CMC: Tokyo, Japan, 1990.
6. (d) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991.
7. (e) Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds. Biomedical Frontiers of Fluorine Chemistry; ACS Symp. Ser. No. 639; American Chemical Society: Washington, DC, 1996.
8. (a) Ondetti, M. A.; Cushman, D. W.; Rubin, B. Science 1977, 196, 441-444.
9. (b) Cushman, D. W.; Cheung, H. S.; Sabo, E. F.; Ondetti, M. A. Biochemistry 1977, 16, 5484-5491.
10. (c) Kollonitsch, J.; Perkins, L. M.; Patchett, A. A.; Doldouras, G. A.; Marburg, S.; Duggan, D. E.; Maycock, A. L.; Aster, S. D. Nature 1978, 274, 906-908.
11. (d) Wyvratt, M. J.; Tristram, E. W.; Ikeler, T. J.; Lohr, N. S.; Joshua, H.; Springer, J. P.; Arison, B. H.; Patchett, A. A. J. Org. Chem. 1984, 49, 2816-2819.
12. Kukhar, V. P.; Soloshonok, V. A. Fluorine-Containing Amino Acids: Synthesis and Properties; John Wiley & Sons: New York, 1995.
13. (a) Abeles, R. H.; Maycock, A. L. Acc. Chem. Res. 1976, 9, 313-319.
14. (b) Kumadaki, I. J. Synth. Org. Chem. Jpn. 1984, 42, 786-793.
15. (c) Faraci, W. S.; Walsh, C. T. Biochemistry 1989, 28, 431-437.
16. (a) Walsh, C. Annu. Rev. Biochem. 1984, 53, 493-535.
17. (b) Bey, P. Ann. Chem. Fr. 1984, 9, 695-702.
18. (c) Seiler, N.; Jung, M. J.; Kock-Weser, J. Pharmacol. Rev. 1984, 36, 111-142.
19. (d) Rathod, A. H.; Tashjian, A. H., Jr.; Abeles, R. H. J. Biol. Chem. 1986, 261, 6461-6469.
20. (e) Ojima, I.; Inoue, T.; Chakravarty, S. J. Fluorine Chem. 1999, 97, 3-10.
21. (a) Uneyama, K. In Enantiocontrolled Synthesis of Fluoro-Organie Compounds; Soloshonok, V. A., Ed.; John Wiley & Sons, Ltd.; Chichester, UK, 1999; pp 391-418.
22. (b) Uneyama, K.; Katagiri, T.; Amii, H. J. Synth. Org. Chem. Jpn. 2002, 60, 1069-1075.
23. Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711-6743.
24. Welch, J. T. Tetrahedron 1987, 43, 3123-3197.
25. (a) Osipov, S. N.; Golubev, A. S.; Sewald, N.; Michel, T.; Kolomiets, A. F.; Burger, K. J. Org. Chem. 1996, 61, 7521-7528.
26. (b) Solosholok, V. A.; Kukhar, V. P. Tetrahedron 1997, 53, 8307.
27. (c) Osipov, S. N.; Bruneau, C.; Picquet, M.; Kolomiets, A. F.; Dixneuf, P. H. Chem. Commun. 1998, 2053-2054.
28. (d) Percy, J. M.; Prime, M. E.; Broadhurst, M. J. J. Org. Chem. 1998, 63, 8049-8051.
29. (e) Amii, H.; Kondo, S.; Uneyama, K. Chem. Commun. 1998, 1845-1846.
30. (f) Gerus, I. I.; Kolomeitsev, A. A.; Kolycheva, M. I.; Kukhar, V. P. J. Fluorine Chem. 2000, 105, 31-33.
31. (g) Fustevo, S.; Bartolomé, A.; Sanz-Cervera, J. F.; Sánchez-Roselló, M.; Soler, J. G.; Ramírez de Arellano, C.; Fuentes, A. S. Org. Lett. 2003, 5, 2523-2526.
32. (a) Watanabe, H.; Hashizume, Y.; Uneyama, K. Tetrahedron Lett. 1992, 33, 4333-4336.
33. (b) Amii, H.; Kishikawa, Y.; Kageyama, K.; Uneyama, K. J. Org. Chem. 2000, 65, 3404-3408.
34. (c) Abe, H.; Amii, H.; Uneyama, K. Org. Lett. 2001, 3, 313-315.
35. (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550.
36. (b) Bravo, P.; Crucianelli, M.; Vergani, B.; Zanda, M. Tetrahedron Lett. 1998, 39, 7771-7774.
37. (c) Crucianelli, M.; Bravo, P.; Arnone, A.; Corradi, E.; Meille, S. V.; Zanda, M. J. Org. Chem. 2000, 65, 2965-2971.
38. (d) Katagiri, T.; Handa, M.; Matsukawa, Y.; Kumar. J. S. D.; Uneyama, K. Tetrahedron: Asymmetry 2001, 12, 1303-1331.
39. (e) Fustereo, S.; Navorro, A.; Pina, B.; Soler, J. G.; Bartolomé, A.; Asensio, A.; Simón, A.; Bravo, P.; Fronza, G.; Volonterio, A.; Zanda, M. Org. Lett. 2001, 3, 2621.
40. (f) Lebouvier, N.; Laroche, C.; Huguenot, F.; Brigaud, T. Tetrahedron Lett. 2002, 43, 2827-2830.
41. (g) Wang, H.; Zhao, X. M.; Li, Y. H.; Lu, L. Org. Lett. 2006, 8, 1379-1381.
42. (h) Li G.-Y.; van der Donk, W. A. Org. Lett. 2007, 9, 41-44.
43. Synthesis of 3,3-difluoroproline derivatives: (a) Hart, B. P.; Coward, J. K. Tetrahedron Lett. 1993, 34, 4917-4920.
44. (b) Shi, G. Q.; Cai, W. L. J. Org. Chem. 1995, 60, 6289-6295.
45. (c) Hart, B. P.; Haile, W. H.; Licato, N. J.; Bolanowska, W. E.; McGuive, J. J.; Coward, J. K. J. Med. Chem. 1996, 39, 56-65.
46. (d) Suzuki, A.; Mae, M.; Amii, H.; Uneyama, K. J. Org. Chem. 2004, 69, 5132-5134.
47. Synthesis of 3-fluoroproline derivatives: (a) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163-3167.
48. (b) Demange, L.; Cluzeau, J.; Menez, A.; Dugave, C. Tetrahedron Lett. 2001, 42, 651-653.
49. (c) Bonini, B. F.; Boschi, F.; Franchini, M. C.; Fochi, M.; Fini, F.; Mazzanti, A. Ricci, A. Synlett 2006, 543-546.
50. Synthesis of 4-fluoroproline and 4,4-difluoroproline derivatives: (a) Smith, E. M.; Swiss, G. F.; Neustadt, B. R.; Gold, E. H.; Sommer, J. A.; Brown, A. D.; Chiu, P. J. S.; Moran, R.; Sybertz, E. J.; Baum, T. J. Med. Chem. 1988, 31, 875-885.
51. (b) Karanewsky, D. S.; Badia, M. C.; Cushman, D. W.; DeForrest, J. M.; Dejneka, T.; Lee, V. G.; Loots, M. J.; Petrillo, E. W. J. Med. Chem. 1990, 33, 1459-1469.
52. (c) Kronenthal, D. R.; Mueller, R. H.; Kuester, P. L.; Kissick, T. P.; Johnson, E. J. Tetrahedron Lett. 1990, 31, 1241-1244.
53. (d) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403-7406.
54. (e) Tolman, V.; Vlasakova, V.; Nemecek, J. J. Fluorine Chem. 1993, 60, 185-191.
55. (f) Avent, A. G.; Bowler, A. N.; Doyle, P. M.; Marchand, C. M.; Young, D. W. Tetrahedron Lett. 1992, 33, 1509-1512.
56. (g) Hudlicky, M. J. Fluorine Chem. 1993, 60, 193-210.
57. (h) Burger, K.; Rudolph, M.; Fehn, S.; Sewald, N. J. Fluorine Chem. 1994, 66, 87-90.
58. (i) Tran, T. T.; Patino, N.; Condom, R.; Frogier, T.; Guedj, R. J. Fluorine Chem. 1997, 82, 125-130.
59. (j) Demange, L.; Menez, A.; Dugave, C. Tetrahedron Lett. 1998, 39, 1169-1172.
60. (k) Konas, D. W.; Coward, J. K. J. Org. Chem. 2001, 66, 8831-8842.
61. (l) Doi, M.; Nishi, Y.; Kiritoshi, N.; Iwata, T.; Nago, M.; Nakano, H.; Uchiyama, S.; Nakazawa, T.; Wakamiya, T.; Kobayashi, Y. Tetrahedron. 2002, 58, 8453-8459.
62. (m) O'Neil, I. A.; Thompson, S.; Kalindjian, S. B.; Jenkins, T. C. Tetrahedron Lett. 2003, 44, 7809-7812.
63. (n) Filosa, R.; Holder, C.; Auberson, Y. P. Tetrahedron Lett. 2006, 47, 8929-8932.
64. (o) Chen, L.; Kim, Y. M.; Kucera, D. J.; Harrison, K. E.; Bahmanyar, S.; Scott, J. M.; Yazbeck, D. J. Org. Chem. 2006, 71, 5468-5473.
65. (p) Hu, S.; Martinez, C. A.; Kline, B.; Yazbeck, D.; Tao, J.; Kucera, D. J. Org. Process Res. Dev. 2006, 10, 650-654.
66. Synthesis of fluoromethyl proline derivatives: (a) Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126.
67. (b) Zhang, X.; Qing, F.-L.; Yang, Y.; Yu, J.; Fu, X.-K. Tetrahedron Lett. 2000, 41, 2953-2955.
68. (c) Qiu, X.-L.; Qing, F.-L. J. Chem. Soc., Perkin Trans. 1 2002, 2052-2057.
69. (d) Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2002, 67, 7162-7164.
70. (e) Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2003, 68, 3614.
71. (f) Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 5201-5206.
72. (a) Golbik, R.; Yu, C.; Weyher-Stingl, E.; Huber, R.; Moroder, L.; Budisa, N.; Schiene-Fischer, C. Biochemistry 2005, 44, 16026-16034.
73. (b) Naduthambi, D.; Zondlo, N. J. J. Am. Chem. Soc. 2006, 128, 12430-12434.
74. (c) Ruzza, P.; Siligardi, G.; Donella-Deana, A.; Calderan, A.; Hussain, R.; Rubini, C.; Cesaro, L.; Osler, A.; Guiotto, A.; Pinna, L. A.; Borin, G. J. Pept. Sci. 2006, 12, 462-471.
75. Staas, D. D.; Savage, K. L.; Sherman, V. L.; Shimp, H. L.; Lyle, T. A.; Tran, L. O.; Wiscount, C. M.; McMasters, D. R.; Sanderson, P. E. J.; Williams, P. D.; Lucas, B. J.; Krueger, J. A.; Lewis, S. D.; White, R. B.; Yu, S.; Wong, B. K.; Kochansky, C. J.; Anari, M. R.; Yan, Y.; Vacca, J. P. Bioorg. Med. Chem. 2006, 14, 6900-6916.
76. (a) Holmgrem, S. K.; Taylor, K. M.; Bretscher, L. E.; Raines, R. T. Nature 1998, 392, 666-667.
77. (b) Malkar, N. B.; Lauer-Fields, J. L.; Borgia, J. A.; Fields, G. B. Biochemistry 2002, 41, 6054-6064.
78. (c) Barth, D.; Musiol, H.-J.; Schuett, M.; Fiori, S.; Milbradt, A. G.; Renner, C.; Moroder, L. Chem. Eur. J. 2003, 9, 3692-3702.
79. (d) Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2003, 125, 9262-9263.
80. (e) Doi, M.; Nishi, Y.; Uchiyama, S.; Nishiuchi, Y.; Nakazawa, T.; Ohkubo, T.; Kobayashi, Y. J. Am. Chem. Soc. 2003, 125, 9922-9923.
81. (f) Persikov, A. V.; Ramshaw, J. A. M.; Kirkpatrick, A.; Brodsky, B. J. Am. Chem. Soc. 2003, 125, 11500.
82. (g) Barth, D.; Milbradt, A. G.; Renner, C.; Moroder, L. ChemBioChem 2004, 5, 79-86.
83. (h) Nishi, Y.; Uchiyama, S.; Doi, M.; Nishiuchi, Y.; Nakazawa, T.; Ohkubo, T.; Kobayashi, Y. Biochemistry 2005, 44, 6034-6042.
84. (i) Doi, M.; Nishi, Y.; Uchiyama, S.; Nishiuchi, Y.; Nishio, H.; Nakazawa, T.; Ohkubo, T.; Kobayashi, Y. J. Pept. Sci. 2005, 11, 609-616.
85. (j) Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 127, 15923-15932.
86. (k) Shoulders, M. D.; Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2006, 128, 8112-8113.
87. (l) Boulègue, C.; Milbradt, A. G.; Renner, C.; Moroder, L. J. Mol. Biol. 2006, 358, 846-856.
88. Kim, W.; McMillan, R. A.; Snyder, J. P.; Conticello, V. P. J. Am. Chem. Soc. 2005, 127, 18121-18132.
89. (a) Eberhardt, E. S.; Panasik, N., Jr.; Raines, R. T. J. Am. Chem. Soc. 1996, 118, 12261-12266.
90. (b) Dzakula, Z.; DeRider, M. L.; Markley, J. L. J. Am. Chem. Soc. 1996, 118, 12796-12803.
91. (c) Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 777-778.
92. (d) Renner, C.; Alefelder, S.; Bae, J. H.; Budisa, N.; Huber, R.; Moroder, L. Angew. Chem., Int. Ed. 2001, 40, 923-925.
93. (e) Improta, R.; Benzi, C.; Barone, V. J. Am. Chem. Soc. 2001, 123, 12568-12577.
94. (f) DeRider, M. L.; Wilkens, S. J.; Waddell, M. J.; Bretscher, L. E.; Weinhold, F.; Raines, R. T.; Markley, J. L. J. Am. Chem. Soc. 2002, 124, 2497-2505.
95. (g) Jenkins, C. L.; Lin, G.; Duo, J.; Rapolu, D.; Guzei, I. A.; Raines, R. T.; Krow, G. R. J. Org. Chem. 2004, 69, 8565-8573.
96. (h) Song, I. K.; Kang, Y. K. J. Phys. Chem. B. 2005, 109, 16982-16987.
97. (i) Thomas, K. M.; Naduthambi, D.; Tririya, G.; Zondlo, N. J. Org. Lett. 2005, 7, 2397-2400.
98. (j) Thomas, K. M.; Naduthambi, D.; Zondlo, N. J. J. Am. Chem. Soc. 2006, 128, 2216-2217.
99. (k) Kim, W.; Hardcastle, K. I.; Conticello, V. P. Angew. Chem., Int. Ed. 2006, 45, 8141-8145.
100. (a) Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett. 1993, 34, 5879-5880.
101. (b) Burger, K.; Windeisen, E.; Pires, R. J. Org. Chem. 1995, 60, 7641-7645.
102. (c) Pires, P.; Burger, K. Synthesis 1996, 1277-1279.
103. (d) Burger, K.; Lange, T.; Pires, R. J. Fluorine Chem. 2000, 102, 317.
104. (e) Schedel, H.; Dmowski, W.; Burger, K. Synthesis 2000, 1681.
105. (f) Burger, K.; Bottcher, C.; Radics, G.; Hennig, L. Tetrahedron Lett. 2001, 42, 3061-3063.
106. (g) Spengler, J.; Schedel, H.; Sieler, J.; Quaedflieg, P. J. L. M.; Broxterman, Q. B.; Duchateau, A. L. L.; Burger, K. Synthesis 2001, 1513-1518.
107. (h) Bottcher, C.; Burger, K. Tetrahedron Lett. 2002, 43, 9711-9714.
108. (i) Radics, G.; Pires, R.; Koksch, B.; El-Kousy, S. M.; Burger, K. Tetrahedron Lett. 2003, 44, 1059-1062.
109. (j) Bottcher, C.; Burger, K. Tetrahedron Lett. 2003, 44, 4223-4226.
110. Some selected papers on the synthetic application of hexafluoroacetone: (a) Burger, K.; Hubl, D.; Gertischke, P. J. Fluorine Chem. 1985, 27, 327-332.
111. (b) Iseki, K.; Nagai, T.; Kobayashi, Y. Chem. Pharm. Bull. 1992, 40, 1346-1348.
112. (c) Ohira, Y.; Taguchi, T.; Iseki, K.; Kobayashi, Y. Chem. Pharm. Bull. 1992, 40, 1647-1649.
113. (d) Iseki, K.; Oishi, S.; Namba, H.; Taguchi, T.; Kobayashi, Y. Chem. Pharm. Bull. 1995, 43, 1897-1901.
114. (e) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681.
115. (f) Wu, Y.; Sabbe, K.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 2002, 12, 1629-1632.
116. (g) Wu, Y.; De Clercq, P.; Vandewalle, M.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 2002, 12, 1633-1636.
117. (h) Anderson, J. T.; Toogood, P. L.; Marsh, E. N. G. Org. Lett. 2002, 4, 4281-4283.
118. (i) Lateef, H.; Mullins, S. T. J. Fluorine Chem. 2000, 104, 167-171.
119. (j) Barbarich, T. J.; Nolan, B. G.; Tsujioka, S.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. J. Fluorine Chem. 2001, 112, 335-342.
120. (k) Nolan, B. G.; Tsujioka, S.; Strauss, S. H. J. Fluorine Chem. 2002, 118, 103-106.
121. Middleton, W. J.; Krespan, C. G. J. Org. Chem. 1965, 30, 1398-1402.
122. (a) Petrov, V. A.; DesMarteau, D. D. J. Fluorine Chem. 1996, 77, 175-181.
123. (b) Petrov, V. A.; Khasnis, D. D. Isr. J. Chem. 1999, 39, 147-150.
124. (c) Petrov, V. A. J. Fluorine Chem. 2000, 106, 25-34.
125. (d) Petrov, V. A. Tetrahedron Lett. 2000, 41, 6959.
126. (e) Petrov, V. A. J. Fluorine Chem. 2001, 109, 123-128.
127. (a) Roberts, J. D.; Hall, G. E.; Middleton, W. J. J. Am. Chem. Soc. 1971, 93, 4778-4781.
128. (b) Steglich, W.; Burger, K.; Duerr, M.; Burgis, E. Chem. Ber. 1974, 107, 1488-1498.
129. (c) Burger, K.; Wassmuth, U.; Penninger, S. J. Fluorine Chem. 1982, 20, 813.
130. (d) Burger, K.; Geith, K.; Hoess, E. Synthesis 1990, 352-356.
131. Short accounts: (a) Uneyama, K.; Amii, H. J. Fluorine Chem. 2002, 114, 127-131.
132. (b) Amii, H.; Uneyama, K. Mg-Promoted Selective C-F Bond Cleavage: A General and Efficient Access to Difluoroenol Silyl Ethers and Their Derivatives. In Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; ACS Symp. Ser. No. 911; American Chemical Society: Washington, DC, 2005; pp. 455-475.
133. (a) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323-1324.
134. (b) Amii, H.; Kobayashi, T.; Uneyama, K. Synthesis 2000, 2001-2003.
135. (c) Amii, H.; Kobayashi, T.; Terasawa, H.; Uneyama, K. Org. Lett. 2001, 3, 3103-3105.
136. (d) Hata, H.; Kobayashi, T.; Amii, H.; Uneyama, K.; Welch, J. T. Tetrahedron Lett. 2002, 43, 6099-6102.
137. (e) Uneyama, K.; Tanaka, H.; Kobayashi, S.; Shioyama, M.; Amii, H. Org. Lett. 2004, 6, 2733-2736.
138. (a) Uneyama K.; Kato T. Tetrahedron Lett. 1998, 39, 587-590.
139. (b) Mae, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2000, 41, 7893-7896.
140. (c) Mae, M.; Matsuura, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2002, 43, 2069-2072.
141. (d) Kobayashi, T.; Nakagawa, T.; Amii, H.; Uneyama, K. Org. Lett. 2003, 5, 4297-4300.
142. (e) Amii, H.; Ichihara, Y.; Nakagawa, T.; Kobayashi, T.; Uneyama, K. Chem. Commun. 2003, 2902-2903.
143. (f) Amii, H.; Kohda, M.; Katagiri, T.; Uneyama, K. J. Fluorine Chem. 2006, 127, 505-509.
144. (a) Prakash, G. K. S.; Hu, J.; Olah, G. A. J. Fluorine Chem. 2001, 112, 355-360.
145. (b) Prakash, G. K. S.; Hu, J.; Alauddin, M. M. J. Fluorine Chem. 2003, 121, 239-243.
146. Guo, Y.; Fujiwara, K.; Uneyama, K. Org. Lett. 2006, 8, 827-829.
147. The standard synthetic approaches to dipeptides: (a) Jones, J. Amino Acid and Peptide Synthesis, 2nd ed.; Oxford University Press: Oxford, UK, 2002.
148. (b) Kusumoto, S. Ed. Experimental Chemistry, 4th ed.; Maruzen: Tokyo, Japan, 1990; No. 22.
149. (c) Hodgson, D. R. W.; Sanderson, J. M. Chem. Soc. Rev. 2004, 33, 422-430.
150. He, B. Y.; Wu, T. J.; Yu, X. Y.; Huang, P. Q. Tetrahedron: Asymmetry 2003, 14, 2101-2108.
151. 3 groups: (a) Collins, D.; Stephens, R.; Tatlow, J. C. J. Fluorine Chem. 1986, 32, 213-227.
152. (b) Burdon, J.; Ezmirly, S. T.; Huckerby, T. N. J. Fluorine Chem. 1988, 40, 283-318.
153. (c) Qian, C. P.; Nakai, T.; Dixon, D. A.; Smart, B. E. J. Am. Chem. Soc. 1990, 112, 4602-4604.
154. (d) van der Puy, M. J. Org. Chem. 1997, 62, 6466-6468.
155. (e) Brisdon, A. K.; Crossley, I. R. Chem. Commun. 2002, 2420-2421.
156. (f) Brisdon, A. K.; Crossley, I. R.; Pritchard, R. G.; Sadig, G.; Warren, J. E. Organometallics 2003, 22, 5534-5542.
157. +, 0.4), 355 (4), 91 (100).