Hypervalent silicon as a reactive site in selective bond-forming processes

Synthesis

Volumn , Issue 11, 2005, Pages 1727-1747

  Rendler, Sebastian ^a   Oestreich, Martin ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Aldol reactions; Allylations; Cross coupling; Organocatalysis; Silicon

Indexed keywords

ALCOHOLS; CARBON; CATALYSIS; CHEMICAL BONDS; ELECTRON TRANSITIONS; ORGANIC CHEMICALS; SILANES;

HYPERVALENT SILICON; REACTIVITY; SELECTIVE BOND-FORMING; SILICON INTERMEDIATES;

SILICON;

ALLYL COMPOUND; CARBON; CARBONYL DERIVATIVE; LEWIS ACID; ORGANOSILICON DERIVATIVE; SILANE DERIVATIVE; SILICON; TRANSITION ELEMENT;

ALDOL REACTION; ALLYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CROSS COUPLING REACTION; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS;

EID: 23044466068     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869949     Document Type: Review

References (159)

1. (a) The Chemistry of Organic Silicon Compounds, Vol. 3; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 2001.
2. (b) The Chemistry of Organic Silicon Compounds, Vol. 2; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998.
3. (c) The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1989.
4. For an excellent treatise of modern organosilicon chemistry, see: Brook, M. A. Silicon in Organic, Organometallic and Polymer Chemistry; Wiley: New York, 2000.
5. Chatgilialoglu, C. Organosilanes in Radical Chemistry; Wiley: Chichester, 2004.
6. (a) Katsukiyo, M.; Hosomi, A. In Main Group Metals in Organic Synthesis, Vol. 2; Yamamoto, H.; Oshima, K., Eds.; Wiley-VCH: Weinheim, 2004, 409.
7. (b) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
8. Kost, D.; Kalikhman, I. In The Chemistry of Organic Silicon Compounds, Vol. 2; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998, 1339.
9. Bassindale, A. R.; Glynn, S. J.; Taylor, P. G. In The Chemistry of Organic Silicon Compounds, Vol. 2; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998, 495.
10. (a) Holmes, R. R. Chem. Rev. 1996, 96, 927.
11. (b) Chuit, C; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371.
12. Gilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733.
13. (a) Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds, Vol. 2; Rappoport, Z.; Apeloig, Y., Eds.; Wiley: Chichester, 1998, 1687.
14. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1989, 1479.
15. Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: London, 1998, 763.
16. (a) Hayashi, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 333.
17. (b) Nishiyama, H.; Itoh, K. In Catalytic Asymmetric Synthesis, 2nd ed.; Wiley: New York, 2000, 111.
18. Riant, M.; Mostefaï, N.; Courmarcel, J. Synthesis 2004, 2943.
19. The oxidative degradation of a carbon-silicon bond into a carbon-oxygen bond also proceeds through hypervalent intermediates. The mechanism is understood accordingly. Although this equivalence of silicon and oxygen is fundamentally important for many synthetic applications, the so-called Tamao-Fleming oxidation is not included in this review: Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
20. Johannsen, M.; Jørgensen, K. A.; Helmchen, G. J. Am. Chem. Soc. 1998, 120, 7637.
21. Mathieu, B.; de Fays, L.; Ghosez, L. Tetrahedron Lett. 2000, 41, 9561.
22. Takasu, K.; Misawa, K.; Yamada, M.; Furuta, Y.; Taniguchi, T.; Ihara, M. Chem. Commun. 2000, 1739.
23. Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199.
24. (a) Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405.
25. (b) Denmark, S. E.; Heemstra, J. R. Jr. Org. Lett. 2003, 5, 2303.
26. (c) Denmark, S. E.; Beutner, G. L.; Wynn, T.; Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774.
27. (a) Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800.
28. (b) Denmark, S. E.; Heemstra, J. R. Jr. Synlett 2004, 2411.
29. Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825.
30. (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
31. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, 299.
32. Carreira, E. M. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.: Springer: Berlin, 1999, 997.
33. (a) Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1981, 37, 2165.
34. (b) Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1983, 39, 999.
35. (a) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1984, 106, 4629.
36. (b) Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1985, 107, 8294.
37. Hosomi, A.; Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411.
38. Kira, M.; Sato, K.; Sakurai, H. J. Org. Chem. 1987, 52, 948.
39. Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 29, 89.
40. Schiffers, R.; Kagan, H. B. Synlett 1997, 1175.
41. (a) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7453.
42. (b) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7457.
43. Malkov, A. V.; Mariani, A.; MacDougall, K. N.; Kočovský, P. Org. Lett. 2004, 6, 2253.
44. Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328, C17.
45. (a) Hosomi, A.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987, 1517.
46. (b) Hayashi, T.; Matsumoto, Y.; Kiyoi, T.; Ito, Y.; Kohra, S.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 29, 5667.
47. (a) Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081.
48. (b) Kira, M.; Sato, K.; Sakurai, H. J. Am. Chem. Soc. 1988, 110, 4599.
49. (c) Account: Sakurai, H. Synlett 1989, 1.
50. (d) Kira, M.; Sato, K.; Sakurai, H. J. Am. Chem. Soc. 1990, 112, 257.
51. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453.
52. Kobayashi, S.; Sugiura, M.; Ogawa, C. Adv. Synth. Catal. 2004, 346, 1023; and references cited therein.
53. Denmark, S. E.; Coe, D. A.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
54. Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
55. Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610.
56. Ogawa, C.; Sugiura, M.; Kobayashi, S. Angew. Chem. Int. Ed. 2004, 43, 6491.
57. Nakajima, M.; Kotani, S.; Ishizuka, T.; Hashimoto, S. Tetrahedron Lett. 2005, 46, 157.
58. (a) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767.
59. (b) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977.
60. (c) For allenylation, see: Iseki, K.; Kuroki, Y.; Kobayashi, Y. Tetrahedron: Asymmetry 1998, 9, 2889.
61. Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S.-i. J. Am. Chem. Soc. 1998, 120, 6419.
62. (a) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047.
63. (b) Malkov, A. V.; Bell, M.; Orsini, M.; Pernazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Kočovský, P. J. Org. Chem. 2003, 68, 9659.
64. Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799.
65. (a) Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827.
66. (b) Malkov, A. V.; Dufková, L.; Farrugia, L.; Koč ovský, P. Angew. Chem. Int. Ed. 2003, 42, 3674.
67. (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.
68. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
69. (c) Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951.
70. Hellwig, J.; Belser, T.; Müller, J. F. K. Tetrahedron Lett. 2001, 42, 5417.
71. Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920.
72. (a) Kubota, K.; Leighton, J. L. Angew. Chem. Int. Ed. 2003, 42, 946.
73. (b) Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 6, 4375.
74. (a) Berger, R.; Rabbat, M. A.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 9596.
75. (b) Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686.
76. Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992, 114, 7922.
77. (a) Denmark, S. E.; Griedel, B. D.; Coe, D. M. J. Org. Chem. 1993, 58, 988.
78. (b) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026.
79. Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59, 7152.
80. Zhang, X.; Houk, K. N.; Leighton, J. L. Angew. Chem. Int. Ed. 2005, 44, 938.
81. Denmark, S. E.; Jacobs, R. T.; Dai-Ho, G.; Wilson, S. Organometallics 1990, 9, 3015.
82. Gilman, H.; Atwell, W. H. J. Am. Chem. Soc. 1964, 86, 2687.
83. (a) Wang, Z.; Wang, D.; Sui, X. Chem. Commun. 1996, 2261.
84. (b) Wang, D.; Wang, Z. G.; Wang, M. W.; Chen, Y. J.; Liu, L.; Zhu, Y. Tetrahedron: Asymmetry 1999, 10, 327.
85. Zhang, L. C.; Sakurai, H.; Kira, M. Chem. Lett. 1997, 129.
86. Schmidt, D. R.; Park, P. K.; Leighton, J. L. Org. Lett. 2003, 5, 3535.
87. Schmidt, D. R.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 1190.
88. (a) Zacuto, M. J.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 8587.
89. (b) O'Malley, S. J.; Leighton, J. L. Angew. Chem. Int. Ed. 2001, 40, 2915.
90. (c) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. Tetrahedron 2003, 59, 8889.
91. Corriu, R. J. P.; Moreau, J. J. E. J. Organomet. Chem. 1976, 120, 337.
92. Cowden, C. J.; Paterson, I. Org. React. (N.Y.) 1997, 51, 1.
93. Account: Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432.
94. (a) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
95. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333.
96. (c) Denmark, S. E.; Winter, S. B. D. Synlett 1997, 1087.
97. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. Tetrahedron 1998, 54, 10389.
98. (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982.
99. α-Chiral aldehydes: (a) Denmark, S. E.; Stavenger, R. A. J. Org. Chem. 1998, 63, 9524.
100. (b) Denmark, S. E.; Fujimori, S. E. Synlett 2001, 1024.
101. (a) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918.
102. (b) Denmark, S. E.; Stavenger, R. A. J. Am. Chem. Soc. 2000, 122, 8837.
103. (c) Denmark, S. E.; Pham, S. M. J. Org. Chem. 2003, 68, 5045.
104. (a) Denmark, S. E.; Su, X.; Nishigaichi, Y. J. Am. Chem. Soc. 1998, 120, 12990.
105. (b) Denmark, S. E.; Pham, S. M. Helv. Chim. Acta 2000, 53, 1846.
106. Denmark, S. E.; Gosh, S. K. Angew. Chem. Int. Ed. 2001, 40, 4895.
107. Recently, a direct organocatalytic enantioselective cross-aldol reaction of aldehydes was reported: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
108. Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
109. (a) Review: Mukaiyama, T. Angew. Chem. Int. Ed. 2004, 43, 5590.
110. (b) Fujisawa, H.; Mukaiyama, T. Chem. Lett. 2002, 182.
111. (c) Fujisawa, H.; Mukaiyama, T. Chem. Lett. 2002, 858.
112. (d) Mukaiyama, T.; Fujisawa, H.; Nakagawa, T. Helv. Chim. Acta 2002, 85, 4518.
113. Nakajima, M.; Yokota, T.; Saito, M.; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61.
114. Nakajima, M.; Orito, Y.; Ishizuka, T.; Hashimoto, S. Org. Lett. 2004, 6, 3763.
115. (a) Denmark, S. E.; Sweis, R. F. In Metal-catalyzed Cross-coupling Reactions, 2nd ed., Vol. 1; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 163.
116. (b) Hiyama, T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 421.
117. (c) Hiyama, T. J. Organomet. Chem. 2002, 653, 58.
118. (d) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835.
119. (e) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull 2002, 12, 1531.
120. (f) Denmark, S. E.; Ober, M. H. Aldrichimica Acta 2003, 36, 75.
121. For leading references, see: (a) Miyaura, N. In Metal-catalyzed Cross-coupling Reactions, 2nd ed., Vol. 1; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 41.
122. (b) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem. Int. Ed. 2003, 42, 4302.
123. (c) Negishi, E.-i.; Liu, F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 1.
124. (d) Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 4704.
125. Echavarren, A. M.; Cárdenas, D. J. In Metal-catalyzed Cross-coupling Reactions, 2nd ed., Vol. 1; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 1.
126. Hatanaka, Y.; Goda, K.; Hiyama, T. J. Organomet. Chem. 1994, 465, 97.
127. Hatanaka, Y.; Hiyama, T. J. Am. Chem. Soc. 1990, 112, 7793.
128. Yoshida, J.-i.; Tamao, K.; Yamamoto, H.; Kakui, T.; Uchida, T.; Kumada, M. Organometallics 1982, 1, 542.
129. (a) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918.
130. (b) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1989, 54, 268.
131. (c) For the related cross-coupling with triflates, see: Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1990, 31, 2719.
132. Matsubashi, H.; Hatanaka, Y.; Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1995, 36, 1539.
133. Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 6051.
134. For the application of bis(catechol) silicates in cross-coupling reactions, see: (a) Hosomi, A.; Kohra, S.; Tominaga, Y. Chem. Pharm. Bull. 1988, 36, 4622.
135. (b) Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 69, 1137.
136. (a) Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 15196.
137. (b) Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2004, 126, 12432.
138. (c) Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102.
139. (d) Denmark, S. E.; Yang, S.-M. Tetrahedron 2004, 60, 9695.
140. Lee, J.-Y.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 5616.
141. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
142. (b) Denmark, S. E.; Wehrli, D.; Choi, J. Y. Org. Lett. 2000, 2, 2491.
143. (a) Itami, K.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 5600.
144. (b) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 11577.
145. For allylic silanes as precursors, see: (a) Nakao, Y.; Oda, T.; Sahoo, A. K.; Hiyama, T. J. Organomet. Chem. 2003, 687, 570.
146. (b) Sahoo, A. K.; Nakao, Y.; Hiyama, T. Chem. Lett. 2004, 33, 632.
147. (c) For thienylsilanes as precursors, see: Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 31, 138.
148. (d) For alkoxysilanes and aqueous base, see: Murata, M.; Shimazaki, R.; Watanabe, S.; Masuda, Y. Synthesis 2001, 2231.
149. Hagiwara, E.; Gouda, K.-i.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439.
150. (a) Denmark, S. E.; Neuville, L. Org. Lett. 2000, 2, 3221.
151. (b) Denmark, S. E.; Pan, W. J. Organomet. Chem. 2002, 653, 98.
152. (c) For an analogous cross-coupling of alkynylsilanols; see: Chang, S.; Yang, S. H.; Lee, P. H. Tetrahedron Lett. 2001, 42, 4833.
153. Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865.
154. (a) Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299.
155. (b) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342.
156. (a) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439.
157. (b) Denmark, S. E.; Tymonko, S. A. J. Org. Chem. 2003, 68, 9151.
158. 3 was also found to be effective: Denmark, S. E.; Ober, M. H. Org. Lett. 2003, 5, 1357.
159. Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2004, 126, 4876.