Dynamic Kinetic Resolutions

Asymmetric Organic Synthesis with Enzymes

Volumn , Issue , 2008, Pages 87-113

  Martín Matute, Belén ^a,b   Bäckvall, Jan E ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Acid catalyzed racemization; Base catalyzed racemization; Dynamic kinetic resolutions; Enzyme catalyzed racemization; Metal catalyzed racemization; Racemization catalyzed by aldehydes; Synthesis of enantiomerically pure compounds; Synthetic applications

Indexed keywords

EID: 84890989094     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527622481.ch4     Document Type: Chapter

References (96)

1. Halpern, J. and Trost, B.M. (2004) Proceedings of the National Academy of Sciences of the United States of America, 101, 5347.
2. Ojima, I. (ed.) (2000) Catalytic Asymmetric Synthesis, 2nd edn, Wiley-VCH Verlag GmbH, New York.
3. Jacobsen, E.N., Pfaltz, A. and Yamamoto, H. (eds) (1999) Comprehensive Asymmetric Catalysis, Springer, Berlin.
4. Noyori, R. (1994) Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, Ltd, New York.
5. Drauz, K. and Waldmann, H. (eds) (2002) Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim, Vols. I-III.
6. Faber, K. (2000) Biotransformations in Organic Chemistry, 4th edn, Springer, Berlin.
7. Dalko, P.I. and Moisan, L. (2004) Angewandte Chemie International Edition, 43, 5138-5175.
8. Knowles, W.S., Sabacky, M.J., Vineyard, B.D. and Weinkauff, D.J. (1975) Journal of the American Chemical Society, 97, 2567-2568.
9. Ohkuma, T. Kitamaura, M. and Noyori, R. (2000) Asymmetric hydrogenations, in Catalytic Asymmetric Synthesis (ed. I. Ojima), 2nd edn, Wiley-VCH Verlag GmbH, New York.
10. Breuer, M., Ditrich, K., Habicher, T., Hauer, B., Keeler, M., Stürmer, R. and Zelinski, T. (2004) Angewandte Chemie International Edition, 43, 788-824.
11. Eliel, E.L., Wilen, S.H. and Mander, L.N. (1994) Stereochemistry of Organic Compounds, John Wiley & Sons, Ltd, New York.
12. Kagan, H.B. and Fiaud, J.C. (1988) Topics in Stereochemistry, 18, 249-330.
13. Sih, C.J. and Wu, S.-H. (1989) Topics in Stereochemistry, 19, 63-125.
14. Chen, C.-S., Wu, S.-H., Girdaukas, G. and Sih, C.J. (1987) Journal of the American Chemical Society, 109, 2812-2817.
15. Chen, C.-S., Fujimoto, Y., Girdaukas, G. and Sih, C.J. (1982) Journal of the American Chemical Society, 104, 7294-7299
16. The selectivity factor used in non-enzymatic kinetic resolutions is known as s, see: reference [6].
17. Martin, V.S., Woodard, S.S., Katsuki, T., Yamada, Y., Ikeda, M. and Sharpless, K.B. (1981) Journal of the American Chemical Society, 103, 6237-6240
18. Bornscheuer, U.T. and Kazlauskas, R.J. (1999) Hydrolases in Organic Synthesis, Wiley-VCH Verlag GmbH, Weinheim.
19. Klibanov, A.M. (2001) Nature, 409, 241-246.
20. Halling, P.J. (2000) Current Opinion in Chemical Biology, 4, 74-80.
21. Zaks, A. and Klibanov, A.M. (1985) Proceedings of the National Academy of Sciences of the United States of America, 82, 3192-3196.
22. Koh, J.H., Jeong, H.M. and Park, J. (1998) Tetrahedron Letters, 39, 5545-5548.
23. Stiirmer, R. (1997) Angewandte Chemie International Edition, 36, 1173-1174.
24. Allen, J.V. and Williams, J.M.J. (1996) Tetrahedron Letters, 37, 1859-1862.
25. Choi, K.L., Suh, J.H., Lee, D., Lim, I.T., Jung, J.Y. and Kim, M.-J. (1999) Journal of Organic Chemistry, 64, 8423-8424.
26. Akai, S., Tanimoto, K., Kanao, Y., Egi, M., Yamamoto, T. and Kita, Y. (2006) Angewandte Chemie International Edition, 45, 2592-2595.
27. Martín-Matute, B., Edin, M., Bogar, K., Kaynak, F.B. and Backvall, J.-E. (2005) Journal of the American Chemical Society, 127, 8817-8825.
28. Clapham, S.E., Hadzovic, A. and Morris, R.H. (2004) Coordination Chemistry Reviews, 248, 2201-2237
29. Gladiali, S. and Alberico, E. (2004) In Transition Metals for Organic Synthesis (eds M. Beller and C. Bolm), 2nd edn, Wiley-VCH Verlag GmbH, Weinheim, Vol. 2, pp. 145-166
30. Backvall, J.-E. (2002) Journal of Organometallic Chemistry, 652, 105-111.
31. Huerta, F.F., Minidis, A.B.E. and Backvall, J.E. (2001) Chemical Society Reviews, 30, 321-331.
32. Wills, M., Palmer, M., Smith, A., Kenny, J. and Walsgrove, T. (2000) Molecules, 5, 4-18.
33. Palmer, M. and Wills, M. (1999) Tetrahedron: Asymmetry, 10, 2045-2061.
34. Martin-Matute, B., Åberg, J.B., Edin, M. and Backvall, J.E. Racemization of Secondary Alcohols Catalyzed by Cyclopentadienyl ruthenium Complexes. Insight into the Reaction Mechanism. Chem. Eur. J. 2007, 13, 6063-6072.
35. Pamies, O. and Backvall, J.-E. (2001) Chemistry-A European Journal, 7, 5052-5058.
36. Samec, J.S.M., Backvall, J.-E., Andersson, P.G. and Brandt, P. (2006) Chemical Society Reviews, 35, 237-248.
37. Dinh, P.M., Howarth, J.A., Hudnott, A.R., Williams, J.M.J. and Harris, W. (1996) Tetrahedron Letters, 37, 7623-7626.
38. Larsson, A.L.E., Persson, B.A. and Backvall, J.-E. (1997) Angewandte Chemie International Edition in English, 36, 1211-1212.
39. Persson, B.A., Larsson, A.L.E., Le Ray, M. and Backvall, J.-E. (1999) Journal of the American Chemical Society, 121, 1645-1650.
40. Menashe, N. and Shvo, Y. (1991) Organometallics, 10, 3885-3891.
41. Verzijl, G.K.M., De Vries, J.G. and Broxterman, Q.B. (2003) PCT International Application WO 0190396 Al 20011129. "Process for preparation of enantiomerically enriched esters and alcohols."
42. Choi, J.E., Kim, Y.H., Nam, S.H., Shin, S.T., Kim, M.J. and Park, J. (2002) Angewandte Chemie International Edition, 41, 2373-2376.
43. Choi, J.H., Choi, Y.K., Kim, Y.H., Park, E.S., Kim, E.J., Kim, M.-J. and Park, J. (2004) Journal of Organic Chemistry, 69, 1972-1977.
44. Martín-Matute, B., Edin, M., Bogar, K. and Backvall, J.-E. (2004) Angewandte Chemie International Edition, 43, 6535-6539
45. DYKAT of 1, 4-symmetrical diols: Martín-Matute, B., Edin, M. and Backvall, J.-E. (2006) Chemistry-A European Journal, 12, 6053-6061.
46. DYKAT of 1, 2-diols: Edin, M., Martín-Matute, B. and Backvall, J.E. (2006) Tetrahedron: Asymmetry, 17, 708-715.
47. DYKATof 3, 5-piperidinediols: Olofsson, B., Bogár, K., Fransson, A.B.L. and Backvall, J.E. (2006) Journal of Organic Chemistry, 71, 8256-8260.
48. Kim, N., Ko, S.-B., Kwon, M.S., Kim, M.-J. and Park, J. (2005) Organic Letters, 7, 4523-4526.
49. Dijksman, A., Elzinga, J.M., Li, Y.-X., Arends, I.W.C.E. and Sheldon, R.A. (2002) Tetrahedron: Asymmetry, 13, 879-884.
50. Kazlauskas, R.J., Weissfloch, A.N.E., Rappaport, A.T. and Cuccia, L.A. (1991) Journal of Organic Chemistry, 56, 2656-2665.
51. S-selective DKR: Kim, M.J., Chung, Y., Choi, Y., Lee, H., Kim, D. and Park, J. (2003) Journal of the American Chemical Society, 125, 11494-11495.
52. Borán, L., Martín-Matute, B., Xu, Y., Córdova, A. and Backvall, J.-E. (2006) Chemistry-A European Journal, 12, 225-232.
53. Berkessel, A., Sebastian-Ibarz, M.L. and Muller, T.N. (2006) Angewandte Chemie International Edition, 45, 6567-6570.
54. Akai, S., Tanimoto, K. and Kita, Y. (2004) Angewandte Chemie International Edition, 43, 1407-1410.
55. van As, B.A.C., van Buijtenen, J., Heise, A., Broxterman, Q.B., Verzjil, G.K.M., Palmans, A.R.A. and Meijer, E.W. (2005) Journal of the American Chemical Society, 127, 9964-9965.
56. Hilker, I., Rabani, G., Verzijl, G.K.M., Palmans, A.R.A. and Heise, A. (2006) Angewandte Chemie International Edition, 45, 2130-2132.
57. Reetz, M.T. and Schimossek, K. (1996) Chimia, 50, 668-669.
58. Paetzold, J. and Backvall, J.-E. (2005) Journal of the American Chemical Society, 127, 17620-17621.
59. Parvulesc, A., De Vos, D. and Jacobs, P. (2005) Chemical Communications, 5307-5309.
60. Stirling, M., Blacker, J. and Page, M.I. (2007) Tetrahedron Letters, 48, 1247-1250.
61. Tan, D.S., Gunter, M.M. and Drueckhammer, D.G. (1995) Journal of the American Chemical Society, 117, 9093-9094.
62. Um, P.-J. and Drueckhammer, D.G. (1998) Journal of the American Chemical Society, 120, 5605-5610.
63. Wen, W.-Y., Ng, I.-S. and Tsai, S.-W. (2006) Journal of Chemical Technology and Biotechnology, 81, 1715-1721.
64. Turner, N.J., Winterman, J.R., McCague, R., Parrat, J.S. and Taylor, S.J.C. (1995) Tetrahedron Letters, 36, 1113-1116.
65. Brown, S.A., Parker, M.-C. and Turner, N.J. (2000) Tetrahedron: Asymmetry, 11, 1687-1690.
66. See also: Bevinakatti, H.S. Newadkar, R.V. and Banerji, A.A. (1990) Journal of the Chemical Society, Chemical Communications, 1091-1092.
67. Bevinakatti, H.S., Banerji, A.A., Newadkar, R.V. and Mokashi, A. (1992) Tetrahedron: Asymmetry, 3, 1505-1508.
68. Gu, R.-L., Lee, I.S. and Sih, C.J. (1992) Tetrahedron Letters, 33, 1953-1956.
69. Crich, J., Brieva, R., Marquart, P., Gu, R.-L., Flemming, S. and Sih, C.J. (1993) Journal of Organic Chemistry, 58, 3252-3258.
70. Suzuki, M., Yamazaki, T., Ohta, H., Shima, K., Ohi, K., Nishiyama, S. and Sugai, T. (2000) Synlett, 189-192.
71. See also: Lo, H.-H., Kao, C.-H., Lee, D.-S., Yang, T.-K. and Hsu, W.-H. (2003) Chirality, 15, 699-702.
72. Taniguchi, T. and Ogasawara, K. (1997) Chemical Communications, 1399-1400.
73. Wuyts, S., De Temmerman, D., De Vos, D. and Jacobs, P.A. (2003) Chemical Communications, 1928-1929.
74. Wuyts, S., De Temmerman, K., De Vos, D.E. and Jacobs, P.A. (2005) Chemistry-A European Journal, 11, 386-397.
75. Ödman, P., Wessjohann, L.A. and Bornscheuer, U.T. (2005) Journal of Organic Chemistry, 70, 9551-9555.
76. Inagaki, M., Hiratake, J., Nishioka, T. and Oda, J. (1992) Journal of Organic Chemistry, 57, 5643-5649.
77. Paizs, C., To§a, M., Majdik, C., Tahinen, P., Irimie, F.-D. and Kanerva, L.T. (2003) Tetrahedron: Asymmetry, 14, 619-627.
78. Paizs, C., Tahinen, P., Lundell, K., Poppe, L., Irimie, F.-D. and Kanerva, L.T. (2003) Tetrahedron: Asymmetry, 14, 1895-1904.
79. Paizs, C., Tahinen, P., To§a, M., Majdik, C., Irimie, F.-D. and Kanerva, L.T. (2004) Tetrahedron, 60, 10533-10540.
80. Veum, L., Kanerva, L.T., Halling, P.J., Maschmeyer, T. and Hanefeld, U. (2005) Advanced Synthesis and Catalysis, 347, 1015-1021.
81. Desantis, G., Zhu, Z., Greenberg, W.A., Wong, K., Chaplin, J., Hanson, S.R., Farwell, B., Nicholson, L.W., Rand, C.L., Weiner, D.P., Robertson, D.E. and Burk, M.J. (2002) Journal of the American Chemical Society, 124, 9024-9025.
82. Brand, S., Jones, M.F. and Rayner, C.M. (1995) Tetrahedron Letters, 36, 8493-8496.
83. Yamada, S., Hongo, C., Yoshioka, R. and Chibata, I. (1982) Journal of Organic Chemistry, 48, 843-846.
84. Chen, S.-T., Huang, W.-H. and Wang, D.-T. (1994) Journal of Organic Chemistry, 59, 7580-7581.
85. Parmar, V.S., Singh, A., Bisht, K.S., Kumar, N., Belokon, Y.N., Kochetkov, K.A., Iknooikov, N.S., Orlova, S.A., Tararov, V.I. and Saveleva, T.F. (1996) Journal of Organic Chemistry, 61, 1223-1227.
86. Hacking, M.A.P.J., Wegman, M.A., Rops, J., van Rantwijk, F. and Sheldon, R.A. (1998) Journal of Molecular Catalysis B: Enzymatic, 5, 155-157.
87. Wegman, M.A., Hacking, M.A.P.J., Rops, J., Pereira, P., Van Rantwijk, F. and Sheldon, R.A. (1999) Tetrahedron: Asymmetry, 10, 1739-1750.
88. Liljeblad, A., Kiviniemi, A. and Kanerva, L.T. (2004) Tetrahedron, 60, 671-677.
89. Asano, Y. and Yamaguchi, S. (2005) Journal of the American Chemical Society, 127, 7696-7697.
90. See also: May, O. Verseck, S. Bommarius, A. and Drauz, D. (2002) Organic Process Research and Development, 6, 452-457.
91. Jones, M.M. and Williams, J.M.J. (1998) Chemical Communications, 2519-2520.
92. Haughton, L. and Williams, J.M.J. (2001) Synthesis, 943-946.
93. Strauss, U.T. and Faber, K. (1999) Tetrahedron: Asymmetry, 10, 4079-4081.
94. Thuring, J.W.J.F., Klunder, A.J.H., Nefkens, G.H.L., Wegman, M.A. and Zwanenburg, B. (1996) Tetrahedron Letters, 37, 4759-4760.
95. Sharfuddin, M., Narumi, A., Iwai, Y., Miyazawa, K., Yamada, S., Kakuchi, t. and Kaga, H. (2003) Tetrahedron: Asymmetry, 14, 1581-1885.
96. Crawford, J.B., Skerlj, R.T. and Bidger, G.J. (2007) Journal of Organic Chemistry, 72, 669-671.