One-pot multi-step synthesis: A challenge spawning innovation

Organic and Biomolecular Chemistry

Volumn 3, Issue 16, 2005, Pages 2899-2906

  Broadwater, Steven J ^a   Roth, Shoshannah L ^a   Price, Kristin E ^a   Kobašlija, Muris ^a   McQuade, D Tyler ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ECONOMIC BENEFITS; ONE-POT MULTI-STEP SYNTHESIS;

CATALYSTS; ECONOMIC AND SOCIAL EFFECTS; ENZYMES;

SYNTHESIS (CHEMICAL);

DRUG; POLYMER;

ARTICLE; CATALYSIS; ENZYME SPECIFICITY; GEL; SYNTHESIS;

CATALYSIS; GELS; PHARMACEUTICAL PREPARATIONS; POLYMERS; SUBSTRATE SPECIFICITY;

EID: 24144483443     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506621m     Document Type: Article

References (155)

1. F. Wohler, Ann. Phys. Chem., 1828, 88.
2. W. A. Greenberg, A. Varvak, S. R. Hanson, K. Wong, H. J. Huang, P. Chen and M. J. Burk, Proc. Natl. Acad. Sci. USA, 2004, 101, 5788-5793.
3. P. T. Anastas and T. C. Williamson, Green chemistry: frontiers in benign chemical synthesis and processes, Oxford University Press, New York, 1998.
4. R. A. Sheldon, J. Chem. Technol. Biotechnol., 1997, 68, 381-388.
5. R. A. Sheldon, Chemtech, 1994, 24, 38-47.
6. N. Bahal and M. C. Nahata, Ann. Pharmacother., 1992, 26, 46-55.
7. W. R. Strohl, Metab. Eng., 2001, 3, 4-14.
8. C. T. Walsh, Science, 2004, 303, 1805-1810.
9. B. M. Trost, Acc. Chem. Res., 2002, 35, 695-705.
10. J. Andraos, Org. Proc. Res. Dev., 2005, 9, 149-163.
11. C. Jimenez-Gonzalez, A. D. Curzons, D. J. C. Constable and V. L. Cunningham, Int. J. Life Cycle Assess., 2004, 9, 114-121.
12. A. E. Marteel, J. A. Davies, W. W. Olson and M. A. Abraham, Annu. Rev. Environ. Resour., 2003, 28, 401-428.
13. P. J. Dunn, S. Galvin and K. Hettenbach, Green Chem., 2004, 6, 43-48.
14. D. J. C. Constable, A. D. Curzons and V. L. Cunningham, Green Chem., 2002, 4, 521-527.
15. M. Eissen and J. O. Metzger, Chem.-Eur. J., 2002, 8, 3580-3585.
16. D. J. C. Constable, A. D. Curzons, L. M. F. dos Santos, G. R. Geen, R. E. Hannah, J. D. Hayler, J. Kitteringham, M. A. McGuire, J. E. Richardson, P. Smith, R. L. Webb and M. Yu, Green Chem., 2001, 3, 7-9.
17. J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302-312.
18. A. Bruggink, R. Schoevaart and T. Kieboom, Org. Proc. Res. Dev., 2003, 7, 622-640.
19. C. Hulme and V. Gore, Curr. Med. Chem., 2003, 10, 51-80.
20. A. M. Hafez, A. E. Taggi, T. Dudding and T. Lectka, J. Am. Chem. Soc., 2001, 123, 10 853-10 859.
21. G. Jas and A. Kirschning, Chem.-Eur. J., 2003, 9, 5708-5723.
22. K. E. Price, S. J. Broadwater, H. M. Jung and D. T. McQuade, Org. Lett., 2005, 7, 147-150.
23. D. J. Ramon and M. Yus, Angew. Chem., Int. Ed., 2005, 44, 1602-1634.
24. F. T. Zimmermann, A. Schneider, U. Schorken, G. A. Sprenger and W. D. Fessner, Tetrahedron: Asymmetry, 1999, 10, 1643-1646.
25. N. J. Turner, Curr. Opin. Biotechnol., 2000, 11, 527-531.
26. C. T. Walsh, Enzymatic Reaction Mechanisms, WH Freeman and Company, New York, 1979.
27. L. E. Manzer, in Benign by Design, P. T. Anastas and C. A. Farris, eds., ACS Symp. Ser. vol. 577, American Chemical Society, Washington, 1994, pp. 144-154.
28. A. Deratani, T. Maraldo, G. D. Darling and J. M. J. Frechet, React. Polym., 1988, 9, 19-28.
29. J. A. Widegren, M. A. Bennett and R. G. Finke, J. Am. Chem. Soc., 2003, 125, 10 301-10 310.
30. J. A. Widegren and R. G. Finke, J. Mol. Catal. A: Chem., 2003, 198, 317-341.
31. J. Rebek and F. Gavina, J. Am. Chem. Soc., 1974, 96, 7112-7114.
32. J. Rebek, D. Brown and S. Zimmerman, J. Am. Chem. Soc., 1975, 97, 454-455.
33. J. Rebek and F. Gavina, J. Am. Chem. Soc., 1975, 97, 1591-1592.
34. J. Rebek, Tetrahedron, 1979, 35, 723-731.
35. I. W. Davies, L. Matty, D. L. Hughes and P. J. Reider, J. Am. Chem. Soc., 2001, 123, 10 139-10 140.
36. R. Grubbs, C. P. Lau, R. Cukier and C. Brubaker, J. Am. Chem. Soc., 1977, 99, 4517-4518.
37. P. Jayalekshmy and S. Mazur, J. Am. Chem. Soc., 1976, 98, 6710-6711.
38. Y. Lin and R. G. Finke, Inorg. Chem., 1994, 33, 4891-4910.
39. M. A. Watzky and R. G Finke, J. Am. Chem. Soc., 1997, 119, 10 382-10 400.
40. J. D. Aiken and R. G. Finke, J. Am. Chem. Soc., 1998, 120, 9545-9554.
41. K. S. Weddle, J. D. Aiken and R. G. Finke, J. Am. Chem. Soc., 1998, 120, 5653-5666.
42. J. A. Widegren, J. D. Aiken, S. Ozkar and R. G. Finke, Chem. Mater., 2001, 13, 312-324.
43. C. M. Hagen, J. A. Widegren, P. M. Maitlis and R. G. Finke, J. Am. Chem. Soc., 2005, 127, 4423-4432.
44. D. E. Bergbreiter, P. L. Osburn and J. D. Frels, Adv. Synth. Catal., 2005, 347, 172-184.
45. K. Q. Yu, W. Sommer, M. Weck and C. W. Jones, J. Catal., 2004, 226, 101-110.
46. K. Q. Yu, W Sommer, J. M. Richardson, M. Week and C. W. Jones, Adv. Synth. Catal., 2005, 347, 161-171.
47. D. R. Anton and R. H. Crabtree, Organometallics, 1983, 2, 855-859.
48. G. M. Whitesides, M. Hackett, R. L. Brainard, J. Lavalleye, A. F. Sowinski, A. N. Izumi, S. S. Moore, D. W. Brown and E. M. Staudt, Organometallics, 1985, 4, 1819-1830.
49. M. N. Vargaftik, V. P. Zagorodnikov, I. P. Stolarov, Il Moiseev, D. I. Kochubey, V. A. Likholobov, A. L. Chuvilin and K. I. Zamaraev, J. Mol. Cat., 1989, 53, 315-348.
50. R. Vanasselt and C. J. Elsevier, J. Mol. Cat., 1991, 65, L13-L19.
51. S. Klingelhofer, W. Heitz, A. Greiner, S. Oestreich, S. Forster and M. Antonietti, J. Am. Chem. Soc., 1997, 119, 10 116-10 120.
52. B. J. Hornstein, J. D. Aiken and R. G. Finke, Inorg. Chem., 2002, 41, 1625-1638.
53. L. N. Lewis and N. Lewis, J. Am. Chem. Soc., 1986, 108, 7228-7231.
54. J. E. Hamlin, K. Hirai, A. Millan and P. M. Maitlis, J. Mol. Catal., 1980, 7, 543-544.
55. S. Hecht and J. M. J. Frechet, Angew. Chem., Int. Ed., 2001, 40, 74-91.
56. F. Gelman, J. Blum and D. Avnir, New J. Chem., 2003, 27, 205-207.
57. F. Gelman, J. Blum and D. J. Avnir, J. Am. Chem. Soc., 2002, 124, 14 460-14 463.
58. F. Gelman, J. Blum, H. Schumann and D. J. Avnir, Sol-Gel Sci. Technol., 2003, 26, 43-46.
59. F. Gelman, J. Blum and D. Avnir, Angew. Chem., Int. Ed., 2001, 40, 3647-3649.
60. P. Furuta, J. Brooks, M. E. Thompson and J. M. Frechet, J. Am. Chem. Soc., 2003, 125, 13 165-13 172.
61. P. Furuta and J. M. J. Frechet, J. Am. Chem. Soc., 2003, 125, 13 173-13 181.
62. S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815-4195.
63. S. V. Ley and I. R. Baxendale, Nat. Rev. Drug Discov., 2002, 1, 573-586.
64. P. H. Toy and K. D. Tanda, Acc. Chem. Res., 2000, 33, 546-554.
65. S. Bhattacharyya, Comb. Chem. High Throughput Screen., 2000, 3, 65-92.
66. B. M. Bhanage and M. Arai, Catal. Rev. Sci. Eng., 2001, 43, 315-344.
67. U. Kragl and T. Dwars, Trends Biotechnol., 2001, 19, 442-449.
68. B. Clapham, T. S. Reger and K. D. Janda, Tetrahedron, 2001, 57, 4637-4662.
69. Q. H. Fan, Y. M. Li and A. S. C. Chan, Chem. Rev., 2002, 102, 3385-3465.
70. Y. Uozumi, in Immobilized Catalysts, A. Kirschning, ed., Springer-Verlag, Berlin, 2004, vol. 242, pp. 77-112.
71. D. E. Bergbreiter, in Immobilized Catalysts, A. Kirschning, ed., Springer-Verlag, Berlin, 2004, vol. 242, pp. 113-176.
72. Y. Hao, M. Andersson, C. Virto, I. Y. Galaev, B. Mattiasson and R. Hatti-Kaul, Biocatal. Biotransform., 2001, 19, 341-359.
73. PdEnCats are highlighted in: N. End, K. U. Schoning, in Immobilized Catalysts, A. Kirschning, ed., Springer-Verlag, Berlin, 2004, vol. 242, pp. 241-271.
74. V. Farina, Adv. Synth. Catal., 2004, 346, 1553-1582.
75. S. Bhattacharyya, Curr. Opin. Drug Discov. Dev., 2004, 7, 752-764.
76. T. J. Dickerson, N. N. Reed and K. D. Janda, Chem. Rev., 2002, 102, 3325-3343.
77. D. J. Gravert and K. D. Janda, Chem. Rev., 1997, 97, 489-509.
78. T. Holletz and D. Cech, Synthesis, 1994, 789-791.
79. F. Sieber, P. Wentworth, J. D. Toker, A. D. Wentworth, W. A. Metz, N. N. Reed and K. D. Janda, J. Org. Chem., 1999, 64, 8058.
80. J. W. Huang and M. Shi, Adv. Synth. Catal., 2003, 345, 953-958.
81. C. A. McNamara, M. J. Dixon and M. Bradley, Chem. Rev., 2002, 102, 3275-3299.
82. A. G. M. Barrett, B. T. Hopkins and J. Kobberling, Chem. Rev., 2002, 102, 3301-3323.
83. E. S. Chandrasekaran, R. H. Grubbs and C. H. Brubaker, J. Organomet. Chem., 1976, 120, 49-63.
84. S. L. Regen and D. P. Lee, Macromolecules, 1977, 10, 1418-1419.
85. S. Nagayama, M. Endo and S. Kobayashi, J. Org. Chem., 1998, 63, 6094-6095.
86. T. Ishida, R. Akiyama and S. Kobayashi, Adv. Synth. Catal., 2003, 345, 576-579.
87. S. Kobayashi and R. Akiyama, Chem. Commun., 2003, 449-460.
88. R. Akiyama and S. Kobayashi, J. Am. Chem. Soc., 2003, 125, 3412-3413.
89. H. Hagio, M. Sugiura and S. Kobayashi, Synlett, 2005, 813-816.
90. K. Okamoto, R. Akiyama and S. Kobayashi, Org. Lett., 2004, 6, 1987-1990.
91. K. Okamoto, R. Akiyama, H. Yoshida, T. Yoshida and S. Kobayashi, J. Am. Chem. Soc, 2005, 127, 2125-2135.
92. The authors of ref. 90 investigated the nature of the PI-Pd catalyst using the three-phase test and conclude that the catalysts are truly heterogeneous. However, the method described by Davies et al. (ref. 35) demonstrates that a solution phase reaction must be performed simultaneously with the heterogeneous reaction. Unfortunately, the authors of ref. 90 did not do this and therefore no conclusion can be made about the nature of the catalytically active species.
93. R. van Heerbeek, P. C. J. Kamer, P. van Leeuwen and J. N. H. Reek, Chem. Rev., 2002, 102, 3717-3756.
94. S. Hecht, J. Polym. Sci. Polym. Chem., 2003, 41, 1047-1058.
95. S. Hecht, N. Vladimirov and J. M. J. Frechet, J. Am. Chem. Soc., 2001, 123, 18-25.
96. E. M. Harth, S. Hecht, B. Helms, E. E. Malmstrom, J. M. J. Frechet and C. J. Hawker, J. Am. Chem. Soc., 2002, 124, 3926-3938.
97. A. Sarkar, P. Ilankumaran, P. Kisanga and J. G. Verkade, Adv. Synth. Catal., 2004, 346, 1093-1096.
98. T. Marquardt and U. Luning, Chem. Commun., 1997, 1681-1682.
99. J. N. H. Reek, D. de Groot, G. E. Oosterom, P. C. J. Kamer and P. van Leeuwen, C. R. Chim., 2003, 6, 1061-1077.
100. Y. Y. Huang, H. L. Zhang, G. J. Deng, W. J. Tang, X. Y. Wang, Y. M. He and Q. H. Fan, J. Mol. Catal. A: Chem., 2005, 227, 91-96.
101. T. Mizugaki, Y. Miyauchi, M. Murata, K. Ebitani and K. Kaneda, Chem. Lett., 2005, 34, 286-287.
102. G. D. Engel and L. H. Gade, Chem.-Eur. J., 2002, 8, 4319-4329.
103. S. Antebi, P. Arya, L. E. Manzer and H. Alper, J. Org. Chem., 2002, 67, 6623-6631.
104. R. Touzani and H. Alper, J. Mol. Catal. A: Chem., 2005, 227, 197-207.
105. P. P. Zweni and H. Alper, Adv. Synth. Catal., 2004, 346, 849-854.
106. K. Heuze, D. Mery, D. Gauss, J. C. Biais and D. Astruc, Chem.-Eur. J., 2004, 10, 3936-3944.
107. D. Astruc, K. Heuze, S. Gatard, D. Mery, S. Nlate and L. Plault, Adv. Synth. Catal., 2005, 347, 329-338.
108. L. K. Yeung and R. M. Crooks, Nano Lett., 2001, 1, 14-17.
109. M. Pittelkow, K. Moth-Poulsen, U. Boas and J. B. Christensen, Langmuir, 2003, 19, 7682-7684.
110. G. Smith, R. Chen and S. Mapolie, J. Organomet. Chem., 2003, 673, 111-115.
111. M. Ooe, M. Murata, A. Takahama, T. Mizugaki, K. Ebitani and K. Kaneda, Chem. Lett., 2003, 32, 692-693.
112. Y. Ribourdouille, G. D. Engel, M. Richard-Plouet and L. H. Gade, Chem. Commun., 2003, 1228-1229.
113. A. M. Arink, R. van de Coevering, B. Wieczorek, J. Firet, J. Jastrzebski, R. Gebbink and G. van Koten, J. Organomet. Chem., 2004, 689, 3813-3819.
114. W. J. Tang, N. F. Yang, B. Yi, G. J. Deng, Y. Y. Huang and Q. H. Fan, Chem. Commun., 2004, 1378-1379.
115. C. Muller, L. J. Ackerman, J. N. H. Reek, P. C. J. Kamer and P. van Leeuwen, J. Am. Chem. Soc., 2004, 126, 14 960-14 963.
116. J. Bu, Z. M. A. Judeh, C. B. Ching and S. Kawi, Catal. Lett., 2003, 85, 183-187.
117. Z. W. Yang, Q. X. Kang, H. C. Ma, C. L. Li and Z. Q. Lei, J. Mol. Catal. A: Chem., 2004, 213, 169-176.
118. B. M. Ji, Y. Yuan, K. L. Ding and A. B. Meng, Chem.-Eur. J., 2003, 9, 5989-5996.
119. T. M. S. Chang, Eur. J. Pharm. Biopharm., 1998, 45, 3-8.
120. H. M. Jung, K. E. Price and D. T. McQuade, J. Am. Chem. Soc., 2003, 125, 5351-5355.
121. K. E. Price and D. T. McQuade, Chem. Commun., 2005, 1714-1716.
122. S. V. Ley, C. Ramarao, A. L. Lee, N. Ostergaard, S. C. Smith and I. M. Shirley, Org. Lett., 2003, 5, 185-187.
123. C. Ramarao, S. V. Ley, S. C. Smith, I. M. Shirley and N. DeAlmeida, Chem. Commun., 2002, 1132-1133.
124. S. V. Ley, C. Ramarao, R. S. Gordon, A. B. Holmes, A. J. Morrison, I. F. McConvey, I. M. Shirley, S. C. Smith and M. D. Smith, Chem. Commun., 2002, 1134-1135.
125. N. Bremeyer, S. V. Ley, C. Ramarao, I. M. Shirley and S. C. Smith, Synlett, 2002, 1843-1844.
126. PdEnCats are highlighted in: D. A. Pears and S. C. Smith, Aldrichimica Acta, 2005, 38, 23-33.
127. J. Q. Yu, H. C. Wu, C. Ramarao, J. B. Spencer and S. V. Ley, Chem. Commun., 2003, 678-679.
128. S. V. Ley, C. Mitchell, D. Pears, C. Ramarao, J. Q. Yu and W. Z. Zhou, Org. Lett., 2003, 5, 4665-4668.
129. L. Sarussi, J. Blum and D. Avnir, J. Sol-Gel Sci. Technol., 2000, 19, 17-22.
130. J. Blum, F. Gelman, R. Abu-Reziq, I. Miloslavski, H. Schumann and D. Avnir, Polyhedron, 2000, 19, 509-512.
131. Z. L. Lu, E. Lindner and H. A. Mayer, Chem. Rev., 2002, 102, 3543-3577.
132. A. S. Bommarius and B. R. Riebel, Biocatalysis, Wiley-VCH, Weinheim, 2004.
133. B. Hauer and S. M. Roberts, Curr. Opin. Chem. Biol., 2004, 8, 103-105.
134. K. A. Powell, S. W. Ramer, S. B. del Cardayre, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp and G. W. Huisman, Angew. Chem., Int. Ed., 2001, 40, 3948-3959.
135. J. R. Cherry and A. L. Fidantsef, Curr. Opin. Biotechnol., 2003, 14, 438-443.
136. M. Adamczak and S. H. Krishna, Food Technol. Biotechnol., 2004, 42, 251-264.
137. S. Lutz, Tetrahedron: Asymmetry, 2004, 15, 2743-2748.
138. A. Ghanem and H. Y. Aboul-Enein, Chirality, 2005, 17, 1-15.
139. N. J. Turner, Curr. Opin. Chem. Biol., 2004, 8, 114-119.
140. J. J. Hao and A. Berry, Protein Eng. Des. Sel., 2004, 17, 689-697.
141. H. J. Lamble, M. J. Danson, D. W. Hough and S. D. Bull, Chem. Commun., 2005, 124-126.
142. A. M. Daines, B. A. Maltman and S. L. Flitsch, Curr. Opin. Chem. Biol., 2004, 8, 106-113.
143. Y. W. Kim, S. S. Lee, R. A. J. Warren and S. G. Withers, J. Biol. Chem., 2004, 279, 42 787-42 793.
144. M. Lafferty and M. J. Dycaico, Methods in Enzymology, 2004, 388, 119-134.
145. J. L. Jestin and P. A. Kaminski, J. Biotechnol., 2004, 113, 85-103.
146. M. T. Reetz, Proc. Natl. Acad. Sci. USA, 2004, 101, 5716-5722.
147. P. A. Dalby, Curr. Opin. Struct. Biol., 2003, 13, 500-505.
148. M. Alexeeva, R. Carr and N. Turner, J. Org. Biomol. Chem., 2003, 1, 4133-4137.
149. K. Hult and P. Berglund, Curr. Opin. Biotechnol., 2003, 14, 395-400.
150. S. Lutz and W. M. Patrick, Curr. Opin. Biotechnol., 2004, 15, 291-297.
151. M. Olsen, B. Iverson and G. Georgiou, Curr. Opin. Biotechnol., 2000, 11, 331-337.
152. F. H. Arnold, Trends Biotechnol., 1990, 8, 244-249.
153. F. H. Arnold, K. Q. Chen, C. Economou, W. Chen, P. Martinez, K. P. Yoon and M. Vandam, in Biocatalyst Design for Stability and Specificity, M. E. Himmel and B. Georgiou, eds., ACS Symp. Ser. vol. 516, American Chemical Society, Washington, 1993, pp. 109-113.
154. F. H. Arnold, Acc. Chem. Res., 1998, 31, 125-131.
155. M. T. Reetz and K. E. Jaeger, in Biocatalysis: from Discovery to Application, W. D. Fessner, ed., Springer-Verlag, Berlin, 1999, vol. 200, pp. 31-57.