Combination of enzymes and metal catalysts. A powerful approach in asymmetric catalysis

Chemical Reviews

Volumn 103, Issue 8, 2003, Pages 3247-3261

  Pàmies, Oscar ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSIS; DYNAMIC KINETIC RESOLUTION; METAL CATALYSTS; TRIACYLGLYCEROL HYDROLASES;

CATALYSIS; CATALYSTS; KINETIC THEORY; REACTION KINETICS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ENZYMES;

EID: 0041878694     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr020029g     Document Type: Article

References (126)

1. (a) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Spring-Verlag: Berlin, 1999.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. (c) Ojima, I. Catalytic Asymmetric Synthesis; VCH: New York, 1993.
4. List, B. Tetrahedron 2002, 58, 5573.
5. (b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
6. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
7. (a) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
8. (b) Faber, K. Biotransformations in Organic Chemistry, 4th ed.; Springer-Verlag: Berlin, 2000.
9. For reviews on DKR, see (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
10. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36.
11. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447.
12. (d) Stecher, H.; Faber, K. Synthesis 1997, 1.
13. (e) Kim, M. J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2002, 13, 578.
14. Analogously, if the nonconverted enantiomer is collected, it is required that conversion is above 50%, which gives a yield below 50%.
15. Michaelis, L.; Menten, M. L. Biochem. Z. 1913, 49, 333.
16. Fersht, A. Enzyme Structure and Mechanism, 2nd ed., Freeman: New York, 1985.
17. Kazlauskas, R. J.; Bornscheuer, U. T. Hydrolases in Organic Chemistry; Wiley-VHC: Weinheim, 1999.
18. (a) Holm, C.; Davis, R. C.; Osterlund, T.; Schotz, M. C.; Fredrikson, G. FEBS Lett. 1994, 344, 234.
19. (b) Luthi-Peng, Q.; Marki, H. P.; Hadvary, P. FEBS Lett. 1992, 299, 111.
20. (c) Martinez, C.; De Geus, P.; Laurewereys, M.; Matthyssens, G.; Cambillau, C. Nature 1992, 356, 615.
21. (d) Brady, L.; Brzozowski, A. M.; Derewenda, Z. S.; Dodson, E.; Dodson, G.; Tolley, S.; Turkenburg, J. P.; Christiansen, L. ; Huge-Jensen, B.; Norskov, L.; Thim, L.; Menge, U. Nature 1990, 343, 767.
22. Winkler, F. K.; Dárcy, A.; Hunziker, N. Nature 1990, 343, 771.
23. (a) Brzozowski, A. M.; Derewenda, U.; Derewenda, Z. S.; Dodson, G. G.; Lawson, D. M.; Turkenburg, J. P.; Björkling, F.; Huge-Jensen, S. A.; Patkar, S. A.; Thim, L. Nature 1991, 351, 491.
24. (b) Schrag, J. D.; Li, Y.; Wu, S.; Cygler, M. Nature 1991, 351, 761.
25. (c) van Tilbeurgh, H.; Egloff, M. P.; Martinez, C.; Rugani, N.; Verger, R.; Cambillau, C. Nature 1993, 362, 814.
26. (d) Grochulski, P.; Li, Y.; Schrag, J. D.; Cygler, M. Protein Sci. 1994, 3, 82.
27. (a) Kraut, J. Annu. Rev. Biochem. 1977, 46, 331.
28. (b) Chulalaksananukul, W.; Condoret, J. S.; Delorme, P.; Willemot, R. M. FEBS Lett. 1990, 276, 181.
29. (c) van Tol, J. B. A.; Jongejan, J. A.; Duine, J. A. Prog. Biotechnol. 1992, 8, 273.
30. (d) Martinelle, M.; Hult, K. Biochim. Biophys. Acta 1995, 1251, 121.
31. (e) Sehanputri, P. S.; Hill, C. G. Biotechnol. Bioeng. 2000, 69, 450.
32. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656.
33. (a) Cygler, M.; Grochulski, P.; Kazlauskas, R. J.; Schrag, J. D.; Bouthillier, F.; Rubin, B.; Serreqi, A. N.; Guptai, A. K . J. Am. Chem. Soc. 1994, 116, 3180.
34. (b) Orrenius, C.; Haffner, F.; Rotticci, D.; Öhrner, N.; Norin, T.; Hult, K. Biocatal. Biotransform. 1998, 16, 1.
35. Ebbers, E. J.; Ariaans, J. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417.
36. See, for instance (a) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook, 2nd ed.; John Wiley & Sons: Weinheim, 2002.
37. (b) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 3rd ed.; John Wiley & Sons: New York, 2001.
38. (c) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, 1999.
39. Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J. E. Chem. Soc. Rev. 2001, 30, 321.
40. (a) Gladiali, S.; Mestroni, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; pp 97-119.
41. (b) Bäckvall, J. E.; Chowdhury, R. L.; Karlsson, U.; Wang, G. Z. In Perspectives in Coordination Chemistry; Williams, A. F., Floriani, C., Merbach, A. E., Eds; Verlag Helvetica Chimica Acta: Basel, 1992; pp 463-486.
42. (c) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
43. Pàmies, O.; Bäckvall, J. E. Chem. Eur. J. 2001, 7, 5052.
44. The question whether the hydride is formed in a concerted manner or via a two step mechanism involving an alkoxide intermediate is still under discussion; see ref 19.
45. (a) Samec, J. S. M.; Bäckvall, J. E. Chem. Eur. J. 2002, 8, 2955.
46. (b) Éll, A. H.; Samec, J. S. M.; Brasse, C.; Bäckvall, J. E. Chem. Commun. 2002, 1144.
47. (a) Granberg, K. L.; Bäckvall, J. E. J. Am. Chem. Soc. 1992, 114, 6858.
48. (b) Bäckvall, J. E.; Granberg, K. L.; Heumann, A. Isr. J. Chem. 1991, 31, 17.
49. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 3543.
50. The mathematical treatment of the kinetics for DKR has been developed. (a) Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853.
51. (b) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144.
52. (a) Krishna, S. H. Biotehnol. Adv. 2002, 20, 239.
53. (b) de Gonzalo, G.; Brieva, R.; Sánchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947.
54. (c) Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
55. (d) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. 2000, 39, 2236.
56. Pámies, O.; Bäckvall, J. E. J. Org. Chem. 2001, 66, 4022. Correctioon: J. Org. Chem. 2002, 67, 1418.
57. Larsson, A. L. E.; Persson, B. A.; Bäckvall, J. E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1211.
58. Strauss, U. T.; Felfer, U.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 107.
59. (a) Fogal, E.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. Tetrahedron: Asymmetry 2000, 11, 2599.
60. (b) Howarth, J.; James, P.; Dai, J. Tetrahedron Lett. 2001, 42, 7517.
61. (c) Dehli, J.; Gotor, V. J. Org. Chem. 2002, 67, 6816.
62. Berezina, N.; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 2002, 13, 1953.
63. (a) Turner, N. J.; Winterman, J. R.; McCague, R.; Parrat, J. S.; Taylor, S. J. Tetrahedron Lett. 1995, 36, 1113.
64. (b) Crich, J.; Brieva, R.; Marqquart, P.; Gu, R. L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252.
65. (c) Brown, S. A.; Parker, M. C.; Turner, M. J. Tetrahedron: Asymmetry 2000, 11, 1687.
66. (d) Chen, C. Y.; Cheng, Y. C.; Tsai, S. W. J. Chem. Technol. Biotechnol. 2002, 77, 699.
67. (a) Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. J. Am. Chem. Soc. 1991, 113, 9360.
68. (b) Brand, S.; Jones, M. F.; Rayner, C. M. Tetrahedron Lett. 1995, 36, 8493.
69. Wegman, M. A.; Hacking, A. P. J.; Rops, J.; Pereira, P.; van Rantwijk, F.; Sheldon, R. A. Tetrahedron: Asymmetry 1999, 10, 1739.
70. (a) Jones, M. M.; Williams, J. M. J. Chem. Commun. 1998, 2519.
71. (b) Haughton, L.; Williams, J. M. J. Synthesis 2001, 943.
72. (c) Badjic, J. D.; Kadnikova, E. N.; Kostic, N. M. Org. Lett. 2001, 3, 2025.
73. Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 42, 7623.
74. Persson, B. A.; Larsson, A. L. E.; Le Ray, M.; Bäckvall, J. E. J. Am. Chem. Soc. 1999. 121, 1645.
75. DKR with isopropenyl acetate using ruthenium catalyst and CALB was already observed in 1997 but not optimized (ref 27).
76. Steinreiber, J. Masters Thesis, Stockholm University, 2002.
77. Koh, J. H.; Jung, H. M.; Kim, M. J.; Park, J. Tetrahedron Lett. 1999, 40, 6281.
78. (a) Jung, H. M.; Koh, J. H.; Kim, M. J.; Park, J. Org. Lett. 2000, 2, 409.
79. (b) Jung, H. M.; Koh, J. H.; Kim, M. J.; Park, J. Org. Lett. 2000, 2, 2487.
80. Dijksman, A.; Elzinga, J. M.; Li, Y. X.; Arends, I. W. C. E; Sheldon, R. A. Tetrahedron: Asymmetry 2002, 13, 879.
81. Verzijl, G. K. M.; De Vries, J. G.; Broxterman, Q. B. WO 0190396 A1 20011129.
82. Choi, J. H.; Kim, Y. H.; Nam, S. H.; Shin, S. T.; Kim, M. J.; Park, J. Angew. Chem., Int. Ed. 2002, 41, 2373.
83. Persson, B. A.; Huerta, F. F.; Bäckvall, J. E. J. Org. Chem. 1999, 64, 5237.
84. Edin, M.; Bäckvall, J. E. J. Org. Chem. 2003, 68, 2216.
85. Kim, M. J.; Choi, Y. K.; Choi, M. Y.; Kim, M. J.; Park, J. J. Org. Chem. 2001, 66, 4736.
86. (a) Huerta, F. F.; Laxmi, Y. R. S.; Bäckvall, J. E. Org. Lett. 2000, 2, 1037.
87. (b) Huerta, F. F.; Bäckvall, J. E. Org. Lett. 2001, 3, 1209.
88. (c) Runmo, A. B. L.; Pàmies, O.; Faber, K.; Bäckvall, J. E. Tetrahedron Lett. 2002, 43, 2983
89. (d) Pàmies, O.; Bäckvall J. E. J. Org. Chem. 2002, 67, 1261.
90. (a) Xiaojun, H.; Corey, E. J. Org. Lett. 2000, 2, 2543.
91. (b) Matsumura, Y.; Fukawa, H.; Chiba, M.; Endo, T. JP 2000139493 2000 (CAN 132: 333456).
92. (c) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem., Int. Ed. 2000, 39, 4308.
93. (d) García, C.; Martín, T.; Martín, V. S. J. Org. Chem. 2001, 66, 1420.
94. (e) Xu, M.-H.; Wang, W.; Xia, L.-J.; Lin, G.-Q. J. Org. Chem. 2001, 66, 3953.
95. (a) Ley, S. V.; Cox, L. R.; Meek, G. Chem. Rev. 1995, 96, 423.
96. (b) Mulzer, J. In Comprehensive Organic Functional Group Transformations; Katrizky, A. R., Meth-Cotn, O., Rees, C. W., Eds.; Elsevier: Oxford, 1995; Vol. 5, pp 121-179.
97. (c) Fukui, H.; Tsuchiya, Y.; Fujita, K.; Nakagawa, T.; Koshino, H.; Nakata, T. Bioorg. Med. Chem. Lett. 1997, 7, 2081.
98. (d) Hsu, J. L.; Chen, C. T.; Fang, J. M. Org. Lett. 1999, 1, 1989.
99. The use of a hydrogen source has also been used by Kim and Park (ref 40).
100. (a) Leffer, J. E.; Temple, R. D. J. Am. Chem. Soc. 1967, 89, 5235.
101. (b) Bosch, I.; Costa, A. M.; Martín, M.; Urpí, F.; Vilarrasa, J. Org. Lett. 2000, 2, 397.
102. (a) Pàmies, O.; Bäckvall, J. E. Adv. Synth. Catal. 2001, 343, 726.
103. (b) Pàmies, O.; Bäckvall, J. E. Adv. Synth. Catal. 2002, 344, 947.
104. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
105. (b) Kordik, C. P.; Reitz, A. B. J. Med. Chem. 1999, 42, 181.
106. (c) Paquette, L. A.; Wang, T. Z.; Pinard, E. J. Am. Chem. Soc. 1996, 117, 1455.
107. Pàmies, O.; Bäckvall, J. E. J. Org. Chem. 2002, 67, 9006.
108. Powell, J. R.; Waimer, I. W.; Drayer, D. E. Drug Stereochemistry Analytical Methods and Pharmacology; Marcel Dekker: New York, 1998.
109. Lee, D.; Huh, E. A.; Kim, M. J.; Jung, H. M.; Koh, J. H.; Park, J. Org. Lett. 2000, 2, 2377.
110. (a) Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1993, 115, 2027.
111. (b) Bäckvall, J. E.; Andreasson, U. Tetrahedron Lett. 1993, 34, 5459.
112. Pàmies, O.; Bäckvall, J. E. J. Org. Chem. 2003, 68, 4815.
113. (a) Guiannousis, P. P.; Barlett, P. A. J. Med. Chem. 1987, 30, 1603.
114. (b) Heilmann, J.; Maier, W. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 471.
115. (c) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
116. (d) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931.
117. (e) Laschat, H.; Kunz, H. Synthesis 1992, 90.
118. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859.
119. Choi, Y. K.; Suh, J. H.; Lee, D.; Lim, I. T.; Jung, J. Y.; Kim, M. J. J. Org. Chem. 1999, 64, 8423.
120. (a) Bäckvall, J. E.; Nordberg, R. E.; Björkman, E. E.; Moberg, C. J. C. S. Chem. Commun. 1980, 943.
121. (b) Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 2301.
122. (c) Bäckvall, J. E.; Nordberg, R. E.; Wilhelm, D. J. Am. Chem. Soc. 1985, 107, 6892
123. Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668.
124. Murahashi, S. I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002.
125. Choi, Y. K.; Kim, M. J.; Ahn, Y.; Kim, M. J. Org. Lett. 2001, 3, 4099.
126. Pàmies, O.; Éll, A. H.; Samec, J. S. M.; Hermanns, N.; Bäckvall, J. E. Tetrahedron Lett. 2002, 43, 4699.