Modern synthetic methods for fluorine-substituted target molecules

Angewandte Chemie - International Edition

Volumn 44, Issue 2, 2004, Pages 214-231

  Shimizu, Masaki ^a,d,e,f   Hiyama, Tamejiro ^a,b,c,d  

^a KYOTO UNIVERSITY   (Japan)

^b HARVARD UNIVERSITY   (United States)

^c SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^d TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^e MITSUBISHI CHEMICAL CORPORATION   (Japan)

^f MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Fluorine; Materials science; Medicinal chemistry; Synthesis design; Synthetic methods

Indexed keywords

AGROCHEMICALS; ARGANOFLUORINE; CHEMICAL PROPERTIES; SUBSTITUENTS;

DRUG PRODUCTS; DYES; ELASTOMERS; FLUORINE; HEAT TRANSFER; LIQUID CRYSTALS; PLASTICS; SUBSTRATES; SURFACE ACTIVE AGENTS; SYNTHESIS (CHEMICAL);

MOLECULES;

ALKANOL; ALKENE DERIVATIVE; FLUORINE; FLUORINE DERIVATIVE; LITHIUM DERIVATIVE; ORGANIC COMPOUND;

ASYMMETRIC SYNTHESIS; CHEMICAL ENGINEERING; DESULFURIZATION; FLUORINATION; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; DRUG DESIGN; STEREOISOMERISM;

CHEMISTRY, AGRICULTURAL; DRUG DESIGN; FLUORINE; ORGANIC CHEMICALS; STEREOISOMERISM;

EID: 11844274689     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460441     Document Type: Review

References (188)

1. a) T. Hiyama, Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000;
2. b) Houben-Weyl, Vol. E10a (Eds.: B. Baasner, H. Hagemann, J. C. Tatlow), Thieme, Stuttgart, 2000;
3. c) Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639 (Eds.: I. Ojima, J. R. McCarthy, J. T. Welch), American Chemical Society, Washington, 1996;
4. d) Chemistry of Organic Fluorine Compounds 11: A Critical Review, ACS Monograph 187 (Eds.: M. Hudlicky, A. E. Pavlath), American Chemical Society, Washington, 1995;
5. e) Organofluorine Chemistry - Principles and Commercial Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum Press, New York, 1994;
6. f) Chemistry of Organic Fluorine Compounds, 2nd ed. (Ed.: M. Hudlicky), Ellis Horwood, New York, 1992;
7. g) Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456 (Ed.: J. T. Welch), American Chemical Society, Washington, 1991;
8. h) Fluorine-containing Molecules: Structure, Reactivity, Synthesis, and Applications (Eds.: J. F. Liebman, A. Greenberg, J. W. R. Dolbier), VCH, New York, 1988;
9. i) J. T. Welch, Tetrahedron 1987, 43, 3123;
10. j) M. Schlosser, Tetrahedron 1978, 34, 3;
11. k) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
12. B. E. Smart, J. Fluorine Chem. 2001, 109, 3.
13. Special issue on "Fluorine in the Life Sciences". ChemBioChem 2004, 5, 557-726.
14. M. Schlosser, Angew. Chem. 1998, 110, 1538; Angew. Chem. Int. Ed. 1998, 37, 1496.
15. M. Schlosser, Angew. Chem. 1998, 110, 1538; Angew. Chem. Int. Ed. 1998, 37, 1496.
16. D. A. Dixon, T. Fukunaga, B. E. Smart, J. Am. Chem. Soc. 1986, 108, 4027.
17. For C-H⋯F interactions, see: a) J. A. K. Howard, V. J. Hoy, D. O'Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613;
18. b) J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89;
19. c) I. Hyla-Kryspin, G. Haufe, S. Grimme, Chem. Eur. J. 2004, 10, 3411;
20. d) J. D. Dunitz, ChemBioChem 2004, 5, 614;
21. for C-M⋯F interactions, see: e) H. Plenio, Chem. Rev. 1997, 97, 3363;
22. f) H. Plenio, ChemBioChem 2004, 5, 65.
23. a) Reference [1b];
24. b) Houben-Weyl, Vol. E10b/1 (Eds.: B. Baasner, H. Hagemann, J. C. Tatlow). Thieme, Stuttgart, 2000;
25. c) Houben-Weyl, Vol. E10b/2 (Eds.: B. Baasner, H. Hagemann, J. C. Tatlow), Thieme, Stuttgart, 2000;
26. d) T. Kitazume, T. Yamazaki, Experimental Methods in Organic Fluorine Chemistry, Kodansha, Tokyo, 1998;
27. e) Top. Curr. Chemi. 1997, 192;
28. f) Top. Curr. Chem. 1997, 193;
29. g) Synthetic Fluorine Chemistry (Eds.: G. A. Olah, R. D. Chambers, G. K. S. Prakash), Wiley, New York, 1992.
30. a) Reference [7a,b];
31. b) J. Hutchinson, G. Sandford, Top. Curr. Chem. 1997, 193, 1;
32. c) J. A. Wilkinson, Chem. Rev. 1992, 92, 505.
33. a) Reference [7b,c];
34. b) J. M. Percy, Top. Curr. Chem. 1997, 193, 131.
35. For a review on halofluorination, see: a) Houben-Weyl, Vol. E10a (Eds.: B. Baasner, H. Hagemann, J. C. Tatlow), Thieme, Stuttgart, 2000, p. 122;
36. b) G. A. Olah, J. T. Welch, Y. D. Vankar, M. Nojima, I. Kerekes, J. A. Olah, J. Org. Chem. 1979, 44, 3872;
37. c) C. York, G. K. S. Prakash, G. A. Olah, J. Org. Chem. 1994, 59, 6493;
38. d) M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn. 1995, 68, 1799.
39. a) G Haufe, Tetrahedron Lett. 1988, 29, 2311;
40. b) C. Saluzzo, G. Alvernhe, D. Anker, G. Haufe, Tetrahedron Lett. 1990, 31, 663.
41. See reference [10b].
42. M. Kuroboshi, K. Kanie, T. Hiyama, Adv. Synth. Catal. 2001, 343, 235.
43. S. Furuta, M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn. 1999, 72, 805.
44. For a review on the synthesis of gem-difluoromethylene compounds, see: M. J. Tozer, T. F. Herpin, Tetrahedron 1996, 52, 8619.
45. M. Kuroboshi, T. Hiyama, Synlett 1991, 909.
46. a) W. B. Motherwell, J. A. Wilkinson, Synlett 1991, 191;
47. b) T. Fuchigami, T. Fujita, J. Org. Chem. 1994, 59, 7190.
48. M. Kuroboshi, T. Hiyama, unpublished results. The Friedel-Crafts acylation of 1,2-dimethoxybenzne with 17, leading to 18, is reported independently: K. Burger, M. Rudolph, H. Neuhauser, Liebigs Ann. Chem. 1991, 1365.
49. M. Kuroboshi, T. Hiyama, unpublished results. The Friedel-Crafts acylation of 1,2-dimethoxybenzne with 17, leading to 18, is reported independently: K. Burger, M. Rudolph, H. Neuhauser, Liebigs Ann. Chem. 1991, 1365.
50. a) M. Kuroboshi, T. Hiyama, Synlett 1994, 251;
51. see also: b) G. S. Lal, E. Lobach, A. Evans, J. Org. Chem. 2000, 65, 4830.
52. K. Kanie, Y. Tanaka, K. Suzuki, M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn. 2000, 73, 471.
53. M. J. Koen, F. I. Guyader, W. B. Motherwell, J. Chem. Soc. Chem. Commun. 1995, 1241.
54. K. Kanie, S. Takehara, T. Hiyama, Bull. Chem. Soc. Jpn. 2000, 73, 1875.
55. a) K. Kanie, K. Mizuno, M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 1973;
56. b) P. Kirsch, M. Bremer, Angew. Chem. 2000, 112, 4384; Angew. Chem. Int. Ed. 2000, 39, 4216.
57. b) P. Kirsch, M. Bremer, Angew. Chem. 2000, 112, 4384; Angew. Chem. Int. Ed. 2000, 39, 4216.
58. For reviews on fluorinated organometallic compounds, see: a) D. J. Burton, Z.-Y. Yang, Tetrahedron 1992, 48, 189;
59. b) D. J. Burton, Z.-Y. Yang, P. A. Morken, Tetrahedron 1994, 50, 2993;
60. c) D. J. Burton, L. Lu, Top. Curr. Chem. 1997, 193, 45.
61. For a Review on the synthesis of pyrethroid acids, see: D. Arlt, M. Jautelat, R. Lantzsch, Angew. Chem. 1981, 93, 719; Angew. Chem. Int. Ed. Engl. 1981, 20, 703.
62. For a Review on the synthesis of pyrethroid acids, see: D. Arlt, M. Jautelat, R. Lantzsch, Angew. Chem. 1981, 93, 719; Angew. Chem. Int. Ed. Engl. 1981, 20, 703.
63. a) M. Fujita, T. Morita, T. Hiyama, Tetrahedron Lett. 1986, 27, 2135;
64. b) M. Fujita, T. Hiyama, Bull. Chem. Soc. Jpn. 1987, 60, 4377.
65. a) R. W. Lang, Helv. Chim. Acta 1986, 69, 881;
66. see also: b) R. W. Lang, Helv. Chim. Acta 1988, 71, 369.
67. D. Bellus, B. Klingert, R. W. Lang, G. Rihs, J. Organomet. Chem. 1988, 339, 17.
68. a) M. Fujita, T. Hiyama, Tetrahedron Lett. 1986, 27, 3655;
69. b) M. Fujita, K. Kondo, T. Hiyama, Bull. Chem. Soc. Jpn. 1987, 60, 4385.
70. a) M. Fujita, T. Hiyama, K. Kondo, Tetrahedron Lett. 1986, 27, 2139;
71. b) reference [29b].
72. a) M. Kuroboshi, N. Yamada, Y. Takebe, T. Hiyama, Synlett 1995, 987;
73. b) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
74. D. J. Burton, J. L. Hahnfeld, J. Org. Chem. 1977, 42, 828.
75. a) T. Hata, M. Shimizu, T. Hiyama, Synlett 1996, 831;
76. b) T. Hata, H. Kitagawa, M. Shimizu, T. Hiyama, Bull. Chem. Soc. Jpn. 2000, 73, 1691.
77. a) O. Yokokoji, T. Shimizu, S. Kumai, JP 08040952, 1996 [Chem. Abstr. 1996, 124, 316586];
78. b) T. Allmendinger, E. Felder, E. Hungerbühler in Selective Fluorination in Organic and Bioorganic Chemistry (Ed.: J. T. Welch), American Chemical Society, Washington, 1991, p. 186;
79. c) P. Bey, J. R. McCarthy, I. A. McDonald in Selective Fluorination in Organic and Bioorganic Chemistry (Ed.: J. T. Welch), American Chemical Society, Washington, 1991, p. 105.
80. a) Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
81. b) Top. Curr. Chem. 2002, 219.
82. a) V. A. Petrov, C. G. Krespan, B. E. Smart, J. Fluorine Chem. 1996, 77, 139;
83. b) J. Weber, L. Xu, U. H. Brinker, Tetrahedron Lett. 1992, 33, 4537;
84. c) S. Eddarir, C. Francesch, H. Mestdagh, C. Rolando, Tetrahedron Lett. 1990, 31, 4449;
85. d) T. Gouyon, R. Sauvetre, J. F. Normant, J. Organomet. Chem. 1990, 394, 37;
86. e) M. Shimizu, G.-H. Cheng, H. Yoshioka, J. Fluorine Chem. 1988, 41, 425;
87. f) T. Fuchikami, I. Ojima, J. Organomet. Chem. 1981, 212, 145.
88. a) M. Shimizu, Y. Takebe, M. Kuroboshi, T. Hiyama, Tetrahedron Lett. 1996, 37, 7387;
89. b) reference [31b].
90. K. Iseki, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1997, 38, 7209.
91. a) A. R. Bassindale, P. G. Taylor in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York. 1989, p. 893;
92. b) J. S. Panek in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming), Pergamon, London, 1991, p. 579.
93. a) M. Shimizu, T. Hata, T. Hiyama, Tetrahedron Lett. 1997, 38, 4591;
94. b) M. Shimizu, T. Hata, T. Hiyama, Tetrahedron Lett. 1999, 40, 7375;
95. c) M. Shimizu, T. Hata, T. Hiyama, Heterocycles 2000, 52, 707:
96. d) M. Shimizu, T. Hata, T. Hiyama, Butt. Chem. Soc. Jpn. 2000, 73, 1685;
97. see also: e) H. Burger, P. Moritz, Organometallics 1993, 12, 4930.
98. B. E. Smart in Organofluorine Chemistry - Principles and Commercial Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994, p. 57.
99. a) I. Fleming in Comprehensive Organic Chemistry, Vol. 3 (Eds.: D. Barton, W. D. Ollis), Pergamon, Oxford, 1979, p. 541;
100. b) A. R. Bassindale, P. G. Taylor, in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1989, p. 951.
101. For examples of vinylsilane products from bis- or tris(triorganosilyl) methanes, see: a) H. Sakurai, K.-i. Nishiwaki, M. Kira, Tetrahedron Lett. 1973, 4193;
102. b) B.-T. Gröbel, D. Seebach, Angew. Chem. 1974, 86, 102; Angew. Chem. Int. Ed. Engl. 1974, 13, 83;
103. b) B.-T. Gröbel, D. Seebach, Angew. Chem. 1974, 86, 102; Angew. Chem. Int. Ed. Engl. 1974, 13, 83;
104. c) B.-T. Grobel, D. Seebach, Chem. Ber. 1977, 110, 852;
105. d) D. Seyferth, J. L. Lefferts, J. R. L. Lambert, J. Organomet. Chem. 1977, 142, 39;
106. e) I. Fleming, C. D. Floyd, J. Chem. Soc. Perkin Trans. 1 1981, 969;
107. f) D. J. Ager, J. Org. Chem. 1984, 49, 168;
108. g) P. F. Hudrlik, E. L. O. Agwaramgbo, A. M. Hudrlik, J. Org. Chem. 1989, 54, 5613;
109. h) C. Palomo, J. M. Aizpurua, J. M. Garcia, I. Ganboa, F. P. Cossio, B. Lecea, C. Lopez, J. Org. Chem. 1990, 55, 2498.
110. a) G. G. Furin, O. A. Vyazankina, B. A. Gostevsky, N. S. Vyazankin, Tetrahedron 1988, 44, 2675;
111. b) T. Hiyama, E. Shirakawa, Top. Curr. Chem. 2002, 219, 61;
112. c) T. Hiyama in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 421.
113. a) G. K. S. Prakash in Synthetic Fluorine Chemistry (Eds.: G. A. Olah, R. D. Chambers, G. K. S. Prakash), Wiley, New York, 1992, p. 227;
114. b) G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757;
115. c) M. Fujita, M. Obayashi, T. Hiyama, Tetrahedron 1988, 44, 4135.
116. For reviews on oxiranyl anions, see: a) T. Satoh, Chem. Rev. 1996, 96, 3303;
117. b) Y. Mori, Rev. Heteroat. Chem. 1997, 17, 183;
118. c) D. M. Hodgson, E. Gras, Synthesis 2002, 1625;
119. see also: d) G. A. Molander, K. Mautner, Pure Appl. Chem. 1990, 62, 707;
120. e) E. Doris, L. Dechoux, C. Mioskowski, Synlett 1998, 337.
121. a) M. Shimizu, T. Fujimoto, H. Minezaki, T. Hata, T. Hiyama, J. Am. Chem. Soc. 2001, 123, 6947;
122. b) M. Shimizu, T. Fujimoto, X. Liu, H. Minezaki, T. Hata, T. Hiyama, Tetrahedron 2003, 59, 9811.
123. It is widely known that β-oxido carbenoids undergo 1,2-rearrangement of a substituent β to the oxygen atom, giving rise to carbonyl compounds; for reviews, see: a) P. M. Wockulich, in Comprehensive Organic Synthesis, Vol. 1 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 873;
124. b) G. Boche, J. C. W. Lohrenz, Chem. Rev. 2001, 101, 697;
125. for examples, see: c) J. Villieras, C. Bacquet, J. F. Normant, J. Organomet. Chem. 1972, 40, C1;
126. d) G. Köbrich, J. Grosser, Tetrahedron Lett. 1972, 4117;
127. e) H. Taguchi, H. Yamamoto, H. Nozaki, Tetrahedron Lett. 1972, 4661;
128. f) G. Köbrich, J. Grosser, Chem. Ber. 1973, 106, 2626;
129. g) J. Villieras, C. Bacquet, J. F. Normant, J. Organomet. Chem. 1975, 97, 325;
130. h) H. Taguchi, H. Yamamoto, H. Nozaki, Bull. Chem. Soc. Jpn. 1977, 50, 1592.
131. Y. Yamauchi, T. Katagiri, K. Uneyama, Org. Lett. 2002, 4, 173.
132. For reviews on oxepanes and oxepins, see: a) D. R. Boyd in Comprehensive Heterocyclic Chemistry, Vol. 7 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, p. 547;
133. b) W. Tochtermann, G. Olsson, Chem. Rev. 1989, 89, 1203;
134. c) L. I. Belen'kii in Comprehensive Heterocyclic Chemistry II, Vol. 9 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, p. 45;
135. d) D. R. Boyd, N. D. Sharma, Chem. Soc. Rev. 1996, 25, 289;
136. e) S. von Angerer, W. Tochtermann in Methods of Organic Chemistry, Vol. E9 (Houben-Weyl), Thieme, Stuttgart, 1998, p. 1.
137. For a review on the Cope rearrangement of bis(alkenyl)oxiranes, see: a) T. Hudlicky, R. Fan, J. W. Reed, K. G. Gadamasetti, Organic Reactions, Vol. 41, Wiley, New York, 1992, p. 1;
138. for examples, see: b) T. Hudlicky, A. Fleming, T. C. Lovelace, Tetrahedron 1989, 45, 3021;
139. c) D. L. Clark, W.-N. Chou, J. B. White, J. Org. Chem. 1990, 55, 3975;
140. d) W.-N. Chou, J. B. White, Tetrahedron Lett. 1991, 32, 157;
141. e) W.-N. Chou, J. B. White, W. B. Smith, J. Am. Chem. Soc. 1992, 114, 4658;
142. f) P. von Zezschwitz, K. Voigt, A. Lansky, M. Noltemeyer, A. de Meijere, J. Org. Chem. 1999, 64, 3806.
143. M. Shimizu, T. Fujimoto, X. Liu, T. Hiyama, Chem. Lett. 2004, 33, 438.
144. Preparation of Alkenes: A Practical Approach (Ed.: J. M. J. Williams), Oxford University Press, Oxford, 1996, p. 1.
145. a) Drugs Fut. 1985, 10, 395;
146. b) Drugs Fut. 1990, 15, 532;
147. c) G. Abraham, T. Horvath, L. Toldy, J. Borvendeg, E. Csanyi, E. Kiss, I. Hermann, S. K. Tory (Gyogyszerkutato Intezet), US 763078, 1989 [Chem. Abstr. 1989, 111, 77630];
148. for biological properties, see: d) J. Borvendeg, I. Hermann, O. Csuka, Acta Physiol Hung. 1996, 84, 405 [Pub Med ID, 1996, 9328614];
149. for biological properties, see: d) J. Borvendeg, I. Hermann, O. Csuka, Acta Physiol Hung. 1996, 84, 405 [Pub Med ID, 1996, 9328614];
150. e) V. Erdelyi-Toth, F. Gyergyay, I. Szamel, E. Pap, J. Kralovanszky, E. Bojti, M. Csorgo, S. Drabant, I. Klebovich, Anti-Cancer Drugs 1997, 8, 603 [Chem. Abstr. 1997, 127, 287616];
151. e) V. Erdelyi-Toth, F. Gyergyay, I. Szamel, E. Pap, J. Kralovanszky, E. Bojti, M. Csorgo, S. Drabant, I. Klebovich, Anti-Cancer Drugs 1997, 8, 603 [Chem. Abstr. 1997, 127, 287616];
152. for the synthesis of panomifene, see: f) G. Nemeth, R. Kapiller-Dezsofi, G. Lax, G. Simig, Tetrahedron 1996, 52, 12821.
153. a) Y. Ukaji, T. Fujisawa, Tetrahedron Lett. 1988, 29, 5165;
154. b) Y. Ukaji, A. Yoshida, T. Fujisawa, Chem. Lett. 1990, 157;
155. c) M. Taniguchi, K. Oshima, K. Utimoto, Tetrahedron Lett. 1991, 32, 2783;
156. d) B. Santiago, C. Lopez, J. A. Soderquist, Tetrahedron Lett. 1991, 52, 3457;
157. e) J. A. Soderquist, C. Lopez, Tetrahedron Lett. 1991, 32, 6305;
158. f) E. Doris, L. Dechoux, C. Mioskowski, Tetrahedron Lett. 1994, 35, 7943;
159. g) E. Doris, L. Dechoux, C. Mioskowski, Tetrahedron Lett. 1994, 35, 7943;
160. h) A. N. Kasatkin, R. J. Whitby, Tetrahedron Lett. 2000, 41, 5275.
161. a) T. Hata, H. Kitagawa, H. Masai, T. Kurahashi, M. Shimizu, T. Hiyama, Angew. Chem. 2001, 113, 812; Angew. Chem. Int. Ed. 2001, 40, 790;
162. a) T. Hata, H. Kitagawa, H. Masai, T. Kurahashi, M. Shimizu, T. Hiyama, Angew. Chem. 2001, 113, 812; Angew. Chem. Int. Ed. 2001, 40, 790;
163. b) M. Shimizu, H. Kitagawa, T. Kurahashi, T. Hiyama, Angew. Chem. 2001, 113, 4283; Angew. Chem. Int. Ed. 2001, 40, 4413;
164. b) M. Shimizu, H. Kitagawa, T. Kurahashi, T. Hiyama, Angew. Chem. 2001, 113, 4283; Angew. Chem. Int. Ed. 2001, 40, 4413;
165. c) M. Shimizu, T. Kurahashi, T. Hiyama, Synlett 2001, 1006;
166. d) T. Kurahashi, T. Hata, H. Masai, H. Kitagawa, M. Shimizu, T. Hiyama, Tetrahedron 2002, 58, 6381;
167. e) M. Shimizu, T. Kurahashi, H. Kitagawa, T. Hiyama, Org. Lett. 2002, 4, 225;
168. f) M. Shimizu, T. Kurahashi, H. Kitagawa, K. Shimono, T. Hiyama, J. Organomet. Chem. 2003, 686, 286.
169. a) M. W. Rathke, R. Kow, J. Am. Chem. Soc. 1972, 94, 6854;
170. b) D. S. Matteson, Synthesis 1975, 147.
171. Triaryl alkenes are one of the key structures of antiestrogens; for reviews on antiestrogens. see: a) R. A. Magadan, L. B. Overacre, S. Singh, K. L. Meyer, Curr. Med. Chem. 1994, 1, 61;
172. b) V. C. Jordan, J. Med. Chem. 2003, 46, 883;
173. c) V. C. Jordan, J. Med. Chem. 2003, 46, 1081.
174. X. Liu, M. Shimizu, T. Hiyama, Angew. Chem. 2004, 115, 897; Angew. Chem. Int. Ed. 2004, 43, 879.
175. X. Liu, M. Shimizu, T. Hiyama, Angew. Chem. 2004, 115, 897; Angew. Chem. Int. Ed. 2004, 43, 879.
176. a) Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions, ACS Symposium Series 746 (Ed.: P. V. Ramachandran), American Chemical Society, Washington, 2000;
177. b) Enantiocontrolled Synthesis of Fluoro-Organic Compounds (Ed.: V. A. Soloshonok), Wiley, Chichester, 1999;
178. c) K. Iseki, Tetrahedron 1998, 54, 13887;
179. d) T. Kitazume, T. Yamazaki, Top. Curr. Chem. 1997, 193, 90;
180. e) P. Bravo, G. Resnati, Tetrahedron: Asymmetry 1990, 1, 661.
181. T. Hiyama, T. Kusumoto, H. Matsutani in Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions, ACS Symposium Series 746 (Ed.: P. V. Ramachandran), American Chemical Society, Washington, 2000, p. 226.
182. H. Poras, H. Matsutani, J. Yaruva, T. Kusumoto, T. Hiyama, Chem. Lett. 1998, 665.
183. H. Matsutani, H. Poras, T. Kusumoto, T. Hiyama, Chem. Commun. 1998, 1259.
184. H. Matsutani, S. Ichikawa, J. Yaruva, T. Kusumoto, T. Hiyama, J. Am. Chem. Soc. 1997, 119, 4541.
185. a) T. Katagiri, H. Ihara, M. Takahashi, S. Kashino, K. Furuhashi, K. Uneyama, Tetrahedron: Asymmetry 1997, 8, 2933;
186. b) T. Katagiri, M. Irie, K. Uneyama, Tetrahedron: Asymmetry 1999, 10, 2583.
187. H. Matsutani, H. Poras, T. Kusumoto, T. Hiyama, Synlett 1998, 1353.
188. H. Matsutani, T, Kusumoto, T. Hiyama, Chem. Lett. 1999, 529.