Polymer-supported organic catalysts

Chemical Reviews

Volumn 103, Issue 9, 2003, Pages 3401-3429

  Benaglia, Maurizio ^a   Puglisi, Alessandra ^a   Cozzi, Franco ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARSONIC ACID; DICYANOKETENE ACETALS; NITROXYL RADICAL; PHASE-TRANSFER CATALYST; PHOSPHONIUM SALTS; POLY N-ISOPROPYLACRYLAMIDE; POLYACRYLAMIDE-SUPPORTED CATALYST; POLYSTYRENE-SUPPORTED CATALYST; PYRIDINIUM SALTS; TRITYL PERCHLORATE;

ACRYLICS; AMINO ACIDS; CATALYSIS; FREE RADICALS; KETONES; MOLECULAR WEIGHT; ORGANIC ACIDS; OXIDATION; POLYETHYLENE GLYCOLS; POLYETHYLENES; POLYSTYRENES; STRUCTURE (COMPOSITION);

CATALYSTS;

EID: 0141619399     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr010440o     Document Type: Article

References (226)

1. Breslow, R. Science 1982, 218, 532.
2. Bickerstaff, G. F. (Ed.) Immobilization of Enzymes and Cells; Humana Press: Totowa, NJ, 1997.
3. Pedersen, S.; Christensen, M. W. Immobilized Biocatalysts. In Applied Biocatalysis, 2nd Edition; Straathof, A. J. J., Adlercreutz, P. Eds.; Harwood Academic Publishers: Amsterdam, 2000; pp 213-228.
4. For an early review on polymeric and supported catalysts see: Manecke, G.; Storck, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 657.
5. De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. In Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, Germany, 2000.
6. An issue of Chemical Reviews (Chem. Rev. 2002, 102, 3215-3892) has recently been devoted to recoverable catalysts and reagents.
7. An issue of Bioorganic & Medicinal Chemistry Lett. (Bioorg. Med. Chem. Lett. 2002, 12, 1791-1884) has recently been devoted to polymer supported catalysts and reagents in synthetic organic chemistry.
8. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815.
9. de Miguel, Y. R.; Brulé, E.; Margue, R. C. J. Chem. Soc., Perkin Trans. 1 2001, 3085.
10. Clapham, B.; Reger, T. S.; Janda, K. Tetrahedron 2001, 57, 4637.
11. For a recent review on the use of dendritic catalysts see: (a) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
12. (b) Twyman, L. J.; King, A. S. H.; Martin, I. K. Chem. Soc. Rev. 2002, 31, 69.
13. For a recent review on the general topic of enantioselective organocatalysis see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
14. Review on dioxirane mediated epoxidation of alkenes: Denmark, S. E.; Wu, Z. Synlett 1999, 847.
15. Review on asymmetric phase-transfer catalysis: Nelson, A. Angew. Chem., Int. Ed. Engl. 1999, 38, 1583.
16. Review on organic catalysis in the Baylis-Hillman reaction: Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
17. Review on the use of proline as an enzyme mimic: Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529.
18. Review on organic catalysis in the Strecker reaction: Yet, L. Angew. Chem., Int. Ed. 2001, 40, 875.
19. Review on organic catalysis in the desymmetrization of cyclic anhydrides: Spivey, A. C.; Andrews, B. I. Angew. Chem., Int. Ed. 2001, 40, 3131.
20. Review on the use of Cinchona alkaloids as organic catalysts: Kacprzak, K.; Gawronski, J. Synthesis, 2001, 961.
21. Review on the use of amino acids and peptides as organic catalysts: Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
22. Song, C. E.; Lee, S. Chem. Rev. 2002, 102, 3495.
23. Lu, Z.; Lindner, E.; Mayer, H. A. Chem. Rev. 2002, 102, 3543.
24. Wight, A. P.; Davis, M. E. Chem. Rev. 2002, 102, 3589.
25. De Vos, D. E.; Dams M.; Sels, B. F.; Jacobs, P. A. Chem. Rev. 2002, 102, 3615.
26. Warshawsky, A. Angew. Makromol. Chem. 1982, 109, 171.
27. Solaro, R.; Dantone, S.; Chiellini React. Polym. 1988, 9, 155.
28. Chakrabarti, A.; Sharma, M. M. React. Polym. 1993, 20, 1.
29. Chesney, A. Green Chem. 1999, 1, 209.
30. Waller, F. J.; Vanscoyoc, R. M. Chemtech 1987, 17, 438.
31. Wulff, G. Chem. Rev. 2002, 102, 1.
32. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis; Chapman & Hall: New York, 1994.
33. Regen, S. L. J. Am. Chem. Soc. 1975, 97, 5956.
34. Regen, S. L. J. Am. Chem. Soc. 1976, 98, 6270.
35. Regen, S. L. Angew. Chem., Int. Ed. Engl. 1979, 18, 421.
36. Regen, S. L. J. Org. Chem. 1977, 42, 875.
37. Chiles, M. S.; Jackson, D. D.; Reeves, P. C. J. Org. Chem. 1980, 45, 2915.
38. Nishikubo, T.; Iizawa, T.; Shimojo, M.; Kato, T.; Shiina, A. J. Org. Chem. 1990, 55, 2536.
39. Cinquini, M.; Colonna, S.; Molinari, H.; Montanari, F.; Tundo, P. Chem. Commun. 1976, 394.
40. Tundo, P. Synthesis 1978, 315.
41. Regen, S. L.; Nigam, A. J. Am. Chem. Soc. 1978, 100, 7773.
42. Molinari, H.; Montanari, F.; Quici, S.; Tundo, P. J. Am. Chem. Soc. 1979, 101, 3920.
43. Regen, S. L.; Besse, J. J. J. Am. Chem. Soc. 1979, 101, 4059.
44. Regen, S. L.; Heh, J. C. K.; McLick, J. J. Org. Chem. 1979, 44, 1961.
45. Fukunishi, K; Czech, B.; Regen, S. L. J. Org. Chem. 1981, 46, 1218.
46. Montanari, F.; Tundo, P. J. Org. Chem. 1981, 46, 2125.
47. Van Zon, A.; de Jong, F.; Onwezen, Y. Recl. Trav. Chim. Pays-Bas 1981, 100, 429.
48. Chung, K. B.; Tomoi, M. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1089.
49. Anelli, P. L.; Montanari, F.; Pollak, V.; Quici, S. Gazz. Chim. Ital. 1986, 116, 127.
50. Although very effective as anion activators, cryptands turned out to be unsuitable for immobilization on chloromethylated polysterene, since the presence of their tertiary nitrogen atoms led to extensive intramolecular quaternization by the unreacted chloromethyl groups of the polymer with concomitant inhibition of the catalytic activity: Anelli, P. L.; Montanari, F.; Quici, S. J. Org. Chem. 1986, 51, 4910.
51. Brown, J. M.; Jenkins, J. A. Chem. Commun. 1976, 458.
52. Tomoi, M.; Ikeda, M.; Kakiuchi, H. Tetrahedron Lett. 1978, 19, 3757.
53. Kondo, S.; Okamura, T.; Takesue, M.; Kunisada, H.; Yuki, Y. Makromol. Chem. 1992, 193, 2265.
54. Regen, S. L.; Dulak, L. J. Am. Chem. Soc. 1977, 99, 623.
55. McKenzie, W. M.; Sherrington, D. C. Chem. Commun. 1978, 541.
56. Yanagida, S.; Takahashi, K.; Okahara, M. J. Org. Chem. 1979, 44, 1099.
57. Kondo, S.; Yamamoto, T.; Mase, M.; Kunisada, H.; Yuki, Y. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1535.
58. Svec, F. Pure Appl. Chem. 1988, 60, 377.
59. Tomoi, M.; Ford, W. T. J. Am. Chem. Soc. 1981, 103, 3821.
60. Tomoi, M.; Ford, W. T. J. Am. Chem. Soc. 1981, 103, 3828.
61. Montanari, F.; Quici, S.; Tundo, P. J. Org. Chem. 1983, 48, 199.
62. Anelli, P. L.; Montanari, F.; Quici, S. J. Chem. Soc., Perkin Trans. 2, 1983, 1827.
63. Anelli, P. L.; Czech, B.; Montanari, F.; Quici, S. J. Am. Chem. Soc. 1984, 106, 861.
64. Ford, W. T.; Tomoi, M. Adv. Polym. Sci. 1984, 55, 49.
65. For reviews on the general problem of reactant accessibility within a polymeric support, see: (a) Guyot, A. Pure Appl. Chem. 1988, 60, 365.
66. (b) Hodge, P. Chem. Soc. Rev. 1997, 26, 417.
67. (c) Hudson, D. J. Comb. Chem. 1999, 1, 333 and 403.
68. (c) Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579.
69. Arrad, O.; Sasson Y. J. Org. Chem. 1989, 54, 4993.
70. Ford, W. T.; Chandran, R.; Turk, H. Pure Appl. Chem. 1988, 60, 395.
71. Bernard, M.; Ford, W. T.; Taylor, T. W. Macromolecules 1984, 17, 1812.
72. Lee, J.-J.; Ford, W. T. J. Org. Chem. 1993, 58, 4070.
73. Lee, J.-J.; Ford, W. T. J. Am. Chem. Soc. 1994, 116, 3753.
74. Kirschning, A.; Altwicker, C.; Dräger, G.; Harders, J.; Hoffmann, N.; Hoffmann, U.; Schönfeld, H.; Solodenko, W.; Kunz, U. Angew. Chem., Int. Ed. 2001, 40, 3995.
75. Regen, S. L.; Mehorotra, A.; Singh, A. J. Org. Chem. 1981, 46, 2182.
76. Tamami, B.; Mahdavi, H. Tetrahedron Lett. 2001, 42, 8721.
77. Tamami, B.; Mahdavi, H. React. Funct. Pol. 2002, 51, 7.
78. Tamami, B.; Mahdavi, H. Tetrahedron Lett. 2002, 43, 6225.
79. Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
80. Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325.
81. Bergbreiter, D. E.; Blanton, J. R. J. Org. Chem. 1985, 50, 5828.
82. Grinberg, S.; Kas'yanov, V.; Srinivas, B. React. Funct. Pol. 1997, 34, 53.
83. For the first report describing the activity of poly(ethylene glycol) itself as phase-transfer catalyst see: Kimura, Y.; Regen, S. L. J. Org. Chem. 1982, 42, 2493.
84. (a) Johansson, G. Bioc. Biophys. Acta 1970, 222, 381.
85. (b) Bückmann, A. F.; Morr, M.; Johansson, G. Macromol. Chem. 1981, 182, 1379.
86. Grinberg, S.; Shaubi, E. Tetrahedron 1991, 47, 2895.
87. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Org. Lett. 2000, 2, 1737. The catalytic ability of the PEG part of 15 was found to be neglibeable in control experiments.
88. For a kinetic study and other synthetic applications of catalyst 15, see: Albanese, D.; Benaglia, M.; Landini, D.; Maia, A.; Lupi, V.; Penso, M. Ind. Eng. Chem. Res. 2002, 41, 4928.
89. The beneficial effect exerted by a PEG chain was also evident in a recent report describing quaternary ammonium salts bound to insoluble polystyrene through a PEG linker: Shibatomi, K.; Nakahashi, T.; Uozumi, Y. Synlett 2000, 1643.
90. Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron Lett. 2002, 43, 3391.
91. Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Ressel, S. J. Org. Chem. 1998, 63, 8628.
92. Lee, J. J.; Ford, W. T.; Moore, J. A.; Li, Y. Macromolecules 1994, 27, 4632.
93. For a review on the use of soluble polymeric analogues of dipolar aprotic solvents as phase transfer cataysts, see: Kondo, S.; Ohta, K.; Inagaki, Y.; Minafuji, M.; Yasui, H.; Nakashima, N.; Iwasaki, M.; Furukawa, K.; Tsuda, K. Pure Appl. Chem. 1988, 60, 387.
94. Jacobson, S. E.; Mares, F.; Zambri, P. M. J. Am. Chem. Soc. 1979, 101, 6938.
95. Jacobson, S. E.; Mares, F.; Zambri, P. M. J. Am. Chem. Soc. 1979, 101, 6946.
96. Murray, R. W. Chem. Rev. 1989, 89, 1187.
97. Shiney, A.; Rajan, P. K.; Sreekumar, K. Polym. Int. 1996, 41, 377.
98. Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839.
99. Song, C. E.; Lim, J. S.; Kim, S. C.; Lee, K.-J.; Chi, D. Y. Chem. Commun. 2000, 2415.
100. Neimann, K.; Neumann, R. Chem. Commun. 2001, 487.
101. Review: De Nooy, A. E. J.; Besemer, A.C.; van Bekkum, H. Synthesis 1996, 1153.
102. For the use of supported TEMPO and related radicals in electrochemical oxidation, see: (a) Deronzier, A.; Limosin, D.; Moutet, J.-C. Electrochim. Acta 1987, 32, 1643.
103. (b) Osa, T.; Akiba, U.; Segawa, I.; Bobbitt, J. M. Chem. Lett. 1988, 1423.
104. (c) MacCorquodale, F.; Crayston, J. A.; Walton, J. C.; Worsfold, D. J. Tetrahedron Lett. 1990, 31, 771.
105. (d) Kashiwagi, Y.; Ono, H.; Osa, T. Chem. Lett. 1993, 257.
106. Miyazawa, T.; Endo, T. J. Polym. Sci. Chem. Ed. 1985, 23, 2487.
107. Miyazawa, T.; Endo, T. J. Mol. Catal. 1988, 49, L31.
108. Tsubokawa, N.; Kimoto, T.; Endo, T. J. Mol. Catal. A: Chem. 1995, 101, 45.
109. Fey, T.; Fischer, H.; Bachmann, S.; Albert, K.; Bolm, C. J. Org. Chem. 2001, 66, 8154, and references therein.
110. Anelli, P. L.; Montanari, F.; Quici, S. Org. Synth. 1990, 69, 212, and references therein.
111. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 2000, 271.
112. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Synlett 2001, 102.
113. Menger, F. M.; Chu, C. H. J. Org. Chem. 1981, 46, 5044.
114. Yoshida, J.; Hashimoto, J.; Kawabata, N. Bull. Chem. Soc. Jpn. 1981, 54, 309.
115. Johnston, R. D.; Marston, C. R.; Krieger, P. E.; Goe, G. L. Synthesis 1988, 393.
116. Li, Z.; Ganesan, A. Synth. Commun. 1998, 28, 3209.
117. Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053.
118. Bergbreiter, D. E.; Mariagnanam, V. M.; Zhang, L. Adv. Mater. 1995, 7, 69.
119. Masaki, Y.; Tanaka, N.; Miura, T. Tetrahedron Lett. 1998, 39, 5799.
120. Tanaka, N.; Masaki, Y. Synlett 1999, 1960.
121. Masaki, Y.; Yamada, T.; Tanaka, N. Synlett 2001, 1311.
122. Hon, Y.-S.; Lee, C. F.; Chen, R.-J.; Szu, P.-H. Tetrahedron 2001, 57, 5991.
123. Mukaiyama, T.; Iwakiri, H. Chem. Lett. 1985, 1363.
124. Tanaka, N.; Masaki, Y. Synlett 1999, 1277.
125. Tanaka, N.; Masaki, Y. Synlett 2000, 406.
126. Ishiara, K.; Hasegawa, A.; Yamamoto, H. Angew. Chem., Int. Ed. 2001, 40, 4077.
127. Ishiara, K.; Hasegawa, A.; Yamamoto, H. Synlett 2002, 1296.
128. Hattori, H. Chem. Rev. 1995, 95, 537.
129. Hierl, M. A.; Gamson, E. P.; Klotz, I. M. J. Am. Chem. Soc. 1979, 101, 6020.
130. Delaney, E. J.; Wood, L. E.; Klotz, I. M. J. Am. Chem. Soc. 1982, 104, 799.
131. Shinkai, S.; Tsuji, H.; Hara, Y.; Manabe, O. Bull. Chem. Soc. Jpn. 1981, 54, 631.
132. Tomoi, M.; Akada, Y.; Kakiuchi, H. Makromol. Chem., Rapid Commun. 1982, 3, 537.
133. Menger, F. M.; McCann, D. J. J. Org. Chem. 1985, 50, 3928.
134. Deratani, A.; Darling, G. D.; Horak, D.; Fréchet, J. M. J. Macromolecules 1987, 20, 767.
135. For another example of polystyrene-supported DMAP, see: Storck, W.; Manecke, G. J. Mol. Catal. 1985, 30, 145.
136. Guendouz, F.; Jacquier, R.; Verducci, J. Tetrahedron 1988, 44, 7095.
137. Bergbreiter, D. E.; Osburn, P. L.; Li C. Org. Lett. 2002, 4, 737.
138. Vaidya, R. A.; Mathias, L. J. J. Am. Chem. Soc. 1986, 108, 5514
139. For a review on the use of poly(4-vinylimidazole) and poly(5-vinylbenzimidazole) in esterolysis reactions, see: Overberger, C. G.; Salamone, J. C. Macromolecules 1969, 2, 217.
140. Schuschardt, U.; Vargas, R. M.; Gelbard, G. J. Mol. Catal. A: Chem. 1996, 109, 37.
141. For the observation of a similar behavior of catalyst 58 in a different reaction, see: Leadbeater, N. E.; van der Pol, C. J. Chem. Soc., Perkin Trans. 1 2001, 2831.
142. Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Invidiata, F. P. Tetrahedron Lett. 2000, 41, 1607.
143. Simpson, J.; Rathbone, D. L.; Billington, D. C. Tetrahedron Lett. 1999, 40, 7031.
144. Subba Rao, Y. V.; De Vos, D. E.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2661.
145. For another recent and highly recyclable basic catalyst supported on MCML-41, see: Demicheli, G.; Maggi, R.; Mazzacani, A.; Righi, P.; Sartori, G.; Bigi, F. Tetrahedron Lett. 2001, 42, 2401.
146. Liu, X.; Verkade, J. G. J. Org. Chem. 1999, 64, 4840.
147. Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326.
148. Stanetty, P.; Kremslehner, M. Tetrahedron Lett. 1998, 39, 811.
149. Blossey, E. C.; Neckers, D. C.; Thayer, A. L.; Schaap, A. P. J. Am. Chem. Soc. 1973, 95, 5820.
150. Benaglia, M.; Danelli, T.; Fabris, F.; Sperandio, D.; Pozzi, G. Org. Lett. 2002, 4, 4229.
151. Saotome, Y.; Endo, T.; Okawara, M. Macromolecules 1983, 16, 881.
152. Karimian, K.; Mohanazadeh, F.; Rezai, S. J. Heterocyclic Chem. 1983, 20, 1119.
153. Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
154. Chiellini, E.; Solaro, R. Chem. Commun. 1977, 231.
155. Colonna, S.; Fornasier, R.; Pfeiffer, U. J. Chem. Soc., Perkin Trans. 1 1978, 8.
156. Kobayashi, N.; Iwai, K. Makromol. Chem. Rapid. Commun. 1981, 2, 105.
157. Hodge, P.; Khoshdel, E.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2205.
158. Chinchilla, R.; Mazòn, P.; Najera, C. Tetrahedron: Asymmetry 2000, 11, 3277.
159. Zhengpu, Z.; Yongmer, W.; Zhen, W.; Hodge, P. React. Funct. Pol. 1999, 41, 37.
160. Thierry, B.; Plaquevent, J.-C.; Cahard, D. Tetrahedron: Asymmetry 2001, 12, 983.
161. Thierry, B.; Perrard, T.; Audouard, C.; Plaquevent, J.-C.; Cahard, D. Synthesis 2001, 1742.
162. Castells, J.; Duñach, E. Chem. Lett. 1984, 1859.
163. Danelli, T.; Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Tetrahedron: Asymmetry 2003, 14, 461.
164. Kobayashi, N.; Iwai, K. J. Am. Chem. Soc. 1978, 100, 7071.
165. The use of high pressure constantly depressed the ee: Sera, A.; Takagi, K.; Katayama, H.; Yamada, H.; Matsumoto, K. J. Org. Chem. 1988, 53, 1157.
166. Kobayashi, N.; Iwai, K. Tetrahedron Lett. 1980, 21, 2167.
167. Danda, H.; Chino, K.; Wake, S. Chem. Lett. 1991, 731.
168. Inagaki, M.; Hiratake, J.; Yamamoto, Y.; Oda, J. Bull. Chem. Soc. Jpn. 1987, 60, 4121.
169. Hodge, P.; Khoshdale, E.; Waterhouse, J.; Frechet, J. M. J. Chem. Soc., Perkin Trans. 1 1985, 2327.
170. Alvarez, R.; Hourdin, M.-A.; Cavè, C.; d'Angelo, J.; Chaminade, P. Tetrahedron Lett. 1999, 40, 7091.
171. Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1971, 44, 3186.
172. Yamashita, T.; Yasueda, H.; Nakamura, N. Chem. Lett. 1974, 585.
173. Yamashita, T.; Yasueda, H.; Miyauchi, Y.; Nakamura, N. Bull. Chem. Soc. Jpn. 1977, 50, 1532.
174. Hermann, K.; Wynberg, H. Helv. Chim. Acta 1977, 60, 2208.
175. For a previous example of immobilization of quinineon a polystyrene matrix, see: Grubhofer, N.; Schleith, L. Naturwissenschaften 1953, 40, 508.
176. Hafez, A. M.; Taggi, A. E.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 10853.
177. Wack, H.; Drury, W. J., III: Taggi, A. E.; Ferraris, D.; Lectka, T. Org. Lett. 1999, 1, 1985.
178. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435.
179. Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
180. For another example of poorly stereoselective addition of thiols to cyclohexenone promoted by a polymeric organic catalyst, see: Yamashita, T.; Kagigaki, E.; Takahashi, N.; Nakamura, N. Makromol. Chem. 1983, 184 675.
181. Oku, J.; Inoue, S. Chem. Commun. 1981, 229-230.
182. Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181.
183. Kim, H. J.; Jackson, W. R. Tetrahedron: Asymmetry 1992, 3, 1421.
184. Song, C. E.; Chun, Y. J.; Kim, J. O. Synth. Comm. 1994, 24, 103.
185. Shvo, Y.; Becker, Y.; Gal, M. Chem. Commun. 1994, 2719.
186. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
187. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496.
188. (a) Benaglia, M.; Celentano, G.; Cozzi, F. Adv. Synth. Catal. 2001, 343, 171.
189. (b) Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. Adv. Synth. Catal. 2002, 344, 533.
190. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395.
191. Kondo, K.; Yamano, T.; Takemoto, K. Makromol. Chem. 1985, 186, 1781.
192. Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. J. Mol. Catal. A: Chem. 2003, 0000.
193. Enders, D.; Seki, A. Synlett 2002, 26.
194. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975.
195. Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329.
196. Clapham, B.; Cho, C.-W.; Janda, K. D. J. Org. Chem. 2001, 66, 868.
197. For a modification of this procedure, see: Cordova, A.; Tremblay, M. R.; Clapham, B.; Janda, K. J. J. Org. Chem. 2001, 66, 5645.
198. Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
199. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
200. Benaglia, M.; Celentano, G.; Cinquini, M.; Puglisi, A.; Cozzi, F. Adv. Synth. Catal. 2002, 344, 149.
201. Selkälä, S. A.; Tois, J.; Pihko, P. M.; Koskinen, A. M. P. Adv. Synth. Catal. 2002, 344, 941.
202. Inoue, S. Adv. Polym. Sci. 1976, 21, 78.
203. Julià, S.; Masana, J.; Vega, J. C. Angew. Chem., Int. Ed. 1980, 19, 929.
204. Julià, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annunziata, R.; Molinari, H. J. Chem. Soc., Perkin Trans. 1 1982, 1317.
205. Colonna, S.; Molinari, H.; Banfi, S.; Julià, S.; Masana, J.; Alvarez, A. Tetrahedron 1983, 39, 1635.
206. Colonna, S.; Molinari, H.; Banfi, S.; Julià, S.; Guixer, J. Tetrahedron 1984, 40, 5207.
207. Ebrahim, S.; Wills, M. Tetrahedron: Asymmetry 1997, 8, 3163.
208. Pu, L. Tetrahedron: Asymmetry 1998, 9, 1457.
209. Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 1215.
210. Nel, R. J. J.; van Heerden, P. S.; van Rensburg, H.; Ferreira, D. Tetrahedron Lett. 1998, 39, 5623.
211. Allen, J. V.; Bergeron, S.; Griffiths, M. J.; Mukherjee, S.; Roberts, S. M.; Williamson, N. M.; Wu, L. E. J. Chem. Soc., Perkin Trans. 1 1998, 3171.
212. Takagi, R.; Shiraki, A.; Manabe, T.; Yoneshige, A.; Hiraga, Y.; Kojima, S.; Ohkata, K. Bull. Chem. Soc. Jpn. 2000, 73, 2115.
213. Itsuno, S.; Sakakura, M.; Ito, K. J. Org. Chem. 1990, 55, 6047.
214. Bentley, P. A.; Bergeron, S.; Cappi, M. W.; Hibbs, D. E.; Hursthouse, M. B.; Nugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. Chem. Commun. 1997, 739.
215. Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501.
216. Bentley, P. A.; Bickley, J. F.; Roberts, S. M.; Steiner, A. Tetrahedron Lett. 2001, 42, 3741.
217. Allen, J. V.; Drauz, K.-H.; Flood, R. W.; Liao, Y. W.; Roberts, S. M.; Skidmore, J. Tetrahedron Lett. 1999, 40, 5417.
218. Cappi, M. W.; Chen, W.-P.; Flood, R. W.; Liao, Y. W.; Roberts, S. M.; Skidmore, J.; Smith, J. A.; Williamson, N. Chem. Commun. 1998, 1159.
219. Bentley, P. A.; Cappi, M. W.; Flood, R. W.; Roberts, S. M.; Smith, J. A. Tetrahedron Lett. 1998, 39, 9297.
220. Bentley, P. A.; Flood, R. W.; Roberts, S. M.; Skidmore, J.; Smith, C. B.; Smith, J. A. Chem. Commun. 2001, 1616.
221. Geller, T.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 1397.
222. Ray, P. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 2001, 149.
223. Flood, R. W.; Geller, T. P.; Petty, S. A.; Roberts, S. M.; Skidmore, J.; Volk, M. Org. Lett. 2001, 3, 683.
224. Tsogoeva, S. B.; Wöltinger, J.; Jost, C.; Reichert, D.; Kühnle, A.; Krimmer, H.-P.; Drauz, K. Synlett 2002, 707.
225. Berkessel, A.; Gasch, N.; Glaubitz, K.; Koch, C. Org. Lett. 2001, 3, 3839.
226. Coffey, P. A.; Drauz, K.-H.; Roberts, S. M.; Skidmore, J.; Smith, J. A. Chem. Commun. 2001, 2330.