Synthesis of gem-difluorinated heterocycles using a difluoropropargyl molecular scaffold

ACS Symposium Series

Volumn 1003, Issue , 2009, Pages 135-162

  Arimitsu, Satoru ^a   Hammond, Gerald B ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CATALYSIS; CYCLOADDITION; ETHERS; KETONES; RHODIUM; SCAFFOLDS;

BASIC CONDITIONS; CROSS COUPLING REACTIONS; FLUORINATED ALCOHOL; ISOQUINOLINONES; MOLECULAR SCAFFOLDS; RHODIUM-CATALYZED; RING CLOSINGS;

CYCLIZATION;

EID: 78649489122     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2009-1003.ch007     Document Type: Conference Paper

References (119)

1. For recent reviews, see: Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, 2004
2. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004.
3. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
4. Acetylene Chemistry; Diederich, F., Stang, P. J., Tykwinski, P. P., Eds.; Wiley-VHC: Weinheim, Germany, 2005.
5. Organometallics in Synthesis: A manual; Schlosser, M., Ed.; John Wiley & Sons, Ltd.: Chichester, 2002.
6. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
7. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 4.
8. For Recent reviews on transition metal catalyzed reaction with alkynes, see: Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
9. Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
10. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
11. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
12. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198.
13. Hammond, G. B. J. Fluorine Chem. 2006, 127, 476-488.
14. Konno, T.; Chae, J.; Miyabe, T.; Ishihra, T. J. Org. Chem. 2005, 70, 10172-10174, and for the other examples see
15. Konno, T.; Chae, J.; Ishihara, T.; Yamanaka, H. J. Org. Chem. 2004, 69, 8258-8265.
16. Konno, T.; Chae, J.; Ishihara, T.; Yamanaka, H. Tetrahedron 2004, 60, 11695-11700.
17. Konno, T.; Daitoh, T.; Noiri, A.; Chae, J.; Ishihara, T.; Yamanaka, Org. Lett. 2004, 6, 933-936.
18. Xu, B.; Hammond, G.B. Angew. Chem. Int. Ed. 2005, 44, 7404-7407.
19. For recent examples see: Miranda, P. O.; Ramirez, M. A.; Martin, V. S.; Padron, J. I. Org. Lett. 2006, 8, 1633-1636.
20. Miura, K.; Wang, D.; Matsumoto, Y.; Hosomi, A. Org. Lett. 2005, 7, 503-505.
21. Wipf, P.; Graham, T. H. J. Org. Chem. 2003, 68, 8798-8807.
22. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482-7483.
23. Audouard, C.; Barsukov, I.; Fawcett, J.; Griffith, G. A.; Percy,J. M.; Pintat, S.; Smith, C. A. Chem. Commun. 2004, 1526-1527.
24. Hanzawa, Y.; Inazawa, K.; Kon, A.; Aoki, H.; Kobayashi, Y. Tetrahedron Lett. 1987, 28, 659-662.
25. Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253-2255.
26. Keh, C. C. K.; Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 4062-4063.
27. Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149-11176.
28. Lin, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042-13043.
29. For initial reports, see: Wang, Z.-G.; Hammond, G. B. J. Org. Chem. 2000, 65, 6547-2255.
30. Kirihara, M.; Takuwa, T.; Takizawa, S.; Momose, T.; Nemoto, H.; Tetrahedron 2000, 56, 8275-8280.
31. Arimitsu, S.; Hammond, G. B. J. Org. Chem. 2006, 71, 8865-8868.
32. Podlech, J.; Maier, T. C. Synthesis 2003, 5, 633-655. and references therein.
33. Arimitsu, S; Jacobsen, J. M.; Hammond, G. B. Tetrahedron Lett. 2007, 48, 1625-1627
34. For a comprehensive discussion, see: For Zn2+: Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209-217.
35. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287-8288.
36. For In3+: Loh, T.-P.; Chua, G.-L. Chem. Commun. 2006, 2739-2749.
37. Alcaide, B.; Almendros, P.; Mart, T. Angew. Chem. Int. Ed. 2006, 45, 4501-4504.
38. Miao, W.; Chung, L. W.; Wu, Y. D. J. Am. Chem. Soc. 2004, 126, 13326-13334.
39. Lin, M. J.; Loh, T. P. J. Am. Chem. Soc. 2003, 125, 13042-13043.
40. Yi, X. H.; Meng, Y.; Hua, X. G.; Li, C. J. J. Org. Chem. 1998, 63, 7472-7480.
41. Miao, W.; Lu, W.; Chan, T. H. J. Am. Chem. Soc. 2003, 125, 2412-2413.
42. Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Tetrahedron 2004, 60, 4227-4235.
43. Miyabe, H.; Naito, T. Org. Biomol. Chem. 2004, 2, 1267-1270.
44. Miyabe, H.; Ueda, M.; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131-134.
45. Miyabe, H.; Nishimura, A.; Ueda, M.; Naito, T. Chem. Commun. 2002, 1454-1455.
46. Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
47. Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky A. R., Eds.: Academic Press: New York, 1983, Vol. 31, 273-344.
48. Nakanishi, K.; Goto, T.; Ito, S.; Natori, S; Nozoe, S., Eds.; Kodansha: Natural Products Chemistry: Tokyo, 1974, Vols. 1-3.
49. Babudri, F.; Cicco, S. R.; Farinola, G. M.; Lopez, L. C.; Naso, F.; Pinto, V. Chem. Commun. 2007, 3756-3758.
50. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076-2080.
51. Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 2, 5277-5288.
52. Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535-3537. and references cited therein.
53. For other examples of 2,5-substituted-3-fluorofurans, see: Sham, H. L.; Batebenner, D. A. J. Chem. Soc., Chem. Commum. 1991, 1134-1135.
54. Xu, W.; Chen, Q.-Y. Org. Biomol. Chem. 2003, 1, 1151-1156
55. Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org. Chem. 1987, 53, 2406-2409.
56. Patel, V. F.; Hardin, J. N.; Mastro, J. M.; Law, K. L.; Zimmermann, J. L.; Ehlhardt, W. J.; Woodland, J. M.; Starling, J. J. Bioconjugate Chem. 1996, 7, 497-510.
57. Zhang, X.; Xia, H.; Dong, X.; Jin, J.; Meng, W.-D.; Qing, F.-L. J. Org. Chem. 2003, 68, 9026-9033.
58. Zhou, W.; Gumina, G.; Chong, Y.; Wang, J.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2004, 47, 3399-3408.
59. Kollmannsberger, C.; Nichols, C.; Bokemeyer, C. Cancer 2006, 106, 1217-1226.
60. Kose, M. F.; Meydanli, M. M.; Tulunay, G. Expert Review of Anticancer Therapy 2006, 6, 437-443.
61. Smith, I. E. Seminars in Oncology 2006, 33 (3, Suppl. 9), S19-S-23.
62. Thigpen, T. Seminars in Oncology 2006, 33 (2, Suppl. 6), S26-S32.
63. Arimitsu, S; Hammond. G. B. J. Org. Chem. 2007, 72, 8559-8561.
64. Arimitsu, S; Jacobsen, J. M.; Hammond, G. B. J. Org. Chem. submitted.
65. Ezquerra, J.; Pedregal, C.; Lamas, C. J. Org. Chem. 1996, 61, 5804-5812.
66. Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162.
67. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966-5968.
68. Qing, F.-L.; Gao, W.-Z.; Ying, J. J. Org. Chem. 2000, 65, 2003-2006.
69. Yamaguchi, Y.; Kobayashi, S.; Wakamiya, T.; Matsubara, Y.; Yoshida, Z. J. Am. Chem. Soc. 2000, 122, 7404-7405.
70. Harrison, T. J.; Dake, G. R. Org. Lett. 2004, 6, 5023-5026.
71. Asao, N.; Yudha S., S.; Nogami, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2005, 44, 5526-5528.
72. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211
73. Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990-6993.
74. Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896-7936.
75. Ma, S.; Yu, S.; Gu, Z. Angew. Chem. Int. Ed. 2006, 45, 200-203.
76. Belting, V.; Krause, N. Org. Lett. 2006, 8, 4489-4492.
77. Liu, B.; Brabander, J. K. D. Org. Lett. 2006, 8, 4907-4910.
78. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409-5412.
79. Antoniotti, S.; Genin, E.; Michelet, V.; Genet, J.-P. J. Am. Chem. Soc. 2005, 127, 9976-9977.
80. Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
81. Bach, T.; Krüger, L. Eur. J. Org. Chem. 1999, 2045-2057.
82. The use of normal silica gel for isolation resulted in the decomposition of the benzyl ether group (Table 5, entry 4 and 5) and in increased difficulty in the separation from by-products (Table 5, entry 6).
83. Similar base-mediated cyclization of gem-difluorohomopropargyl alcohols was reported. This report claimed that 3-fluoro-2,5-substituted furans were obtained via a 3-exo-tet cyclization. See reference 21a.
84. El-Taeb, G. M. M.; Evans A. B.; Jones, S.; Knight, D. W. Tetrahedron Lett. 2001, 42, 5945-5948.
85. Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1991, 56, 1685-1687.
86. Marshall. J. A.; Dubay, W. J. J. Am. Chem. Soc. 1992, 114, 1450-1456.
87. Jacobsen, J. M.; Arimitsu, S; Hammond, G. B.; Mashuta, M. S., Acta Cryst. E. 2007, E63, o4337.
88. Liu, J.; Birzin, E. T.; Chan, W.; Yang, Y. T.; Pai, L.-Y.; DaSilva, C.; Hayes, E. C.; Mosley, R. T.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. Bioorg. Med. Chem. Lett. 2005, 15, 715-518.
89. Ennis, M. D.; Ghazal, N. B.; Hoffman, R. L.; Smith, M. W.; Schlachter, S. K.; Lawson, C. F.; Im, W. B.; Pregenzer, J. F.; Svensson, K. A.; Lewis, R. A.; Hall, E. D.; Sutter, D. M.; Harris, L. T.; McCall, R. B. J. Med. Chem. 1998, 41, 2180-2183.
90. Markaryan, E. A.; Samodurova, A. G. Russian Chemical Reviews, 1989, 58, 479-493.
91. For theoretical studies related to [2+2+2] cycloaddition, see: Dahy, A. A.; Suresh, C. H.; Koga, N. Bull. Chem. Soc. Jpn. 2005, 78, 792-803.
92. Dahy, A. A.; Koga, N. Bull. Chem. Soc. Jpn. 2005, 78, 781-791.
93. Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003, 125, 11721-11729.
94. Yamamoto, Y.; Kinpara, K.; Saigoku, T.; Takagishi, H.; Okuda, S.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 605-613.
95. Yamamoto, Y.; Ishii, J.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 9625-9631.
96. Hanazawa, Y.; Kawagoe, K.; Inazawa, K.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 5665-5666.
97. Taguchi, T.; Kitagawa, O.; Morikawa, T.; Nishiwaki, T.; Uehara, H.; Endo, H.; Kobayashi, Y. Tetrahedron Lett. 1986, 27, 6103-6106.
98. Arimitsu, S.; Fernández, B.; del Pozo, C.; Fustero, S.; Hammond, G. B. J. Org. Chem. 2008, 73, in press.
99. For reviews of hydroamination see: Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
100. Nakamura, I.; Yamamoto, Y.; Chem. Rev. 2004, 104, 2127-2198.
101. Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079-3160.
102. Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935-946.
103. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
104. Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
105. Müller, T.; Beller, M. Chem. Rev. 1998, 98, 675-704.
106. Chianese, A. R.; Lee, S. J.; Gagné, M. R. Angew. Chem. Int. Ed. 2007, 46, 4042-4059 and references cited therein.
107. Fustero, S.; Fernández, B.; Bello, P.; del Pozo, C.; Arimitsu, S.; Hammond, G. B. Org. Lett. 2007, 9, 4251-4253.
108. Other sources of paladium were also screened, such us Pd(PPh3)4, PdCl2(PPh3)2, Pd2(dba)3 CHCl3 . The reaction was also performed with other bases (K2CO3), solvents (DMF, DCM), temperatures and reaction times. In all these cases less satisfactory results were obtained.
109. The stereochemistry of the β-lactams was determined by NOESY experiments over the diastereomeric mixture of compounds (Z)-20b +-20b, that were unseparable by flash chromatography.
110. Jacobson, S.; Carty, A. J.; Mathew, M.; Palemik, G. J. J. Am. Chem. Soc. 1974, 96, 4330-4332.
111. McGinnety, J. A. J. Chem. Soc. Dalton Trans. 1974, 1038-1043.
112. Deák, G.; Dóda, M.; György, L.; Hazai, L.; Sterk, L. J. Med. Chem. 1977, 20, 1384-1388.
113. Philippe, N.; Deniviet, F.; Vasse, J.-L.; Santos, J. S. O.; Levacher, V.; Dupas, G. Tetrahedron. 2003, 59, 8049-8056.
114. Amat, M.; Pérez, M.; Minaglia, A. T.; Casamitjana, N.; Bosch, J. Org. Lett. 2005, 7, 3653-3656.
115. "Ene-yne Metathesis" M. Mori, Handbook of Metathesis, Vol. 2 (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003, p. 176.
116. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
117. Poulsen, C. S.; Madsen, R. Synthesis 2003, 1, 1-18.
118. Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083.
119. Hong, S. K.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161.