Metals and Metal Complexes in Cooperative Catalysis with Enzymes within Organic-Synthetic One-Pot Processes

Cooperative Catalysis: Designing Efficient Catalysts for Synthesis

Volumn , Issue , 2015, Pages 325-350

  Gröger, Harald ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Chemoenzymatic synthesis; Cofactor recycling; Dynamic kinetic resolutions; Enzyme catalysis; Metal catalysis; One pot processes

Indexed keywords

CATALYSIS; ENZYMES; METAL COMPLEXES; REACTION INTERMEDIATES; REDOX REACTIONS; SYNTHETIC METALS;

CHEMO-ENZYMATIC SYNTHESIS; CO-FACTOR RECYCLING; DYNAMIC KINETIC RESOLUTION; ENZYME CATALYSIS; METAL CATALYSIS; ONE POT PROCESS;

METALS;

EID: 84991282306     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527681020.ch11     Document Type: Chapter

References (75)

1. Sheldon, R.A., Arends, I., and Hanefeld, U. (2007) Green Chemistry and Catalysis, Chapter 1, Wiley-VCH Verlag GmbH, Weinheim, pp. 1-47.
2. German Catalysis Society, ProcessNet (2010) Roadmap for Catalysis Research in Germany: Catalysis-A Key Technology for Sustainable Economic Growth, 3rd edn.
3. Beller, M. and Bolm, C. (eds) (2008) Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, vols. 1-2, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.
4. Drauz, K., Gröger, H., and May, O. (eds) (2012) Enzyme Catalysis in Organic Synthesis, vols. 1-3, 3rd edn, Wiley-VCH Verlag GmbH, Weinheim.
5. Bruggink, A., Schoevaart, R., and Kieboom, T. (2003) Org. Proc. Res. Dev., 7, 622-640.
6. Pàmies, O. and Bäckvall, J.-E. (2003) Chem. Rev., 103, 3247-3261.
7. Hussain, I. and Bäckvall, J.-E. (2012) in Enzyme Catalysis in Organic Synthesis, Chapter 43, vol. 2, 3rd edn (eds K. Drauz, H. Gröger, and O. May), Wiley- VCH Verlag GmbH, Weinheim, pp. 1777-1806.
8. Denard, C.A., Hartwig, J.F., and Zhao, H. (2013) ACS Catal., 3, 2856-2864.
9. Gröger, H. and Hummel, W. (2014) Curr. Opin. Chem. Biol., 19, 171-179.
10. Weckbecker, A., Gröger, H., and Hummel, W. (2010) Adv. Biochem. Eng./Biotechnol., 120, 195-242.
11. Wu, H., Tian, C., Song, X., Liu, C., Yang, D., and Jiang, Z. (2013) Green Chem., 15, 1773-1789.
12. Westerhausen, D., Herrmann, S., Hummel, W., and Steckhan, E. (1992) Angew. Chem., 104, 1496-1498
13. Angew. Chem., Int. Ed. Engl., (1992), 31, 1529-1531
14. Hollmann, F., Kleeb, A., Otto, K., and Schmid, A. (2005) Tetrahedron: Asymmetry, 16, 3512-3519.
15. Hollmann, F., Schmid, A., and Steckhan, E. (2001) Angew. Chem. Int. Ed., 40, 169-171.
16. Hollmann, F., Witholt, B., and Schmid, A. (2002) J. Mol. Catal. B: Enzym., 19, 167-176.
17. Lo, H.C., Leiva, C., Buriez, O., Kerr, J.B., Olmstead, M.M., and Fish, R.H. (2001) Inorg. Chem., 40, 6705-6716.
18. Wagenknecht, P.S., Penney, J.M., and Hembre, R.T. (2003) Organometallics, 22, 1180-1182.
19. Hummel,W., Kuzu, M., and Geueke, B. (2003) Org. Lett., 5, 3649-3650.
20. Geueke, B., Riebel, B., and Hummel, W. (2003) Enzymol. Microb. Technol., 32, 205-211.
21. Hummel, W. and Riebel, B. (2003) Biotechnol. Lett., 25, 51-54.
22. Hilt, G., Lewall, B., Montero, G., Utley, J.H.P., and Steckhan, E. (1997) Liebigs Ann., 2289-2296.
23. Schröder, I., Steckhan, E., and Liese, A. (2003) J. Electroanal. Chem., 541, 109-115.
24. Maid, H., Böhm, P., Huber, S.M., Bauer, W., Hummel, W., Jux, N., and Gröger, H. (2011)Angew. Chem., 123, 2445-2448
25. Angew. Chem. Int. Ed., (2011), 50, 2397-2400
26. Greschner,W., Lanzerath, C., Reß, T., Tenbrink, K., Borchert, S., Mix, A., Hummel, W., and Gröger, H. (2014) J. Mol. Catal. B: Enzym., 103, 10-15.
27. Allen, J.V. and Williams, J.M.J. (1996) Tetrahedron Lett., 37, 1859-1862.
28. Dinh, P.M., Howarth, J.A., Hudnott, A.R., Williams, J.M.J., and Harris, W. (1996) Tetrahedron Lett., 37, 7623-7626.
29. Larsson, A.L.E., Persson, B.A., and Bäckvall, J.E. (1997) Angew. Chem., 109, 1256-1258
30. Angew. Chem., Int. Ed. Engl., (1997), 36, 1211-1212.
31. Persson, B.A., Larsson, A.L.E., Le Ray, M., and Bäckvall, J.E. (1999) J. Am. Chem. Soc., 121, 1645-1650.
32. Choi, J.H., Kim, Y.H., Nam, S.H., Shin, S.T., Kim, M.J., and Park, J. (2002) Angew. Chem., 114, 2479-2482
33. Angew. Chem. Int. Ed., (2002), 41, 2373-2376.
34. Ko, S.B., Baburaj, B., Kim, M.J., and Park, J. (2007) J. Org. Chem., 72, 6860-6864.
35. Martín-Matute, B., Edin, M., Bogár, K., and Bäckvall, J.-E. (2004) Angew. Chem., 116, 6697-6701; Angew. Chem. Int. Ed., (2004), 43, 6535-6539.
36. Angew. Chem. Int. Ed., (2004), 43, 6535-6539
37. Verzijl, G.K.M., DeVries, J.G., and Broxtermann, Q.B. (2001) process for the preparation of enantiomerically enriched esters and alcohols WO2001090396.
38. Hoyos, P., Fernández, M., Sinisterra, J.V., and Alcántara, A.R. (2006) J. Org. Chem., 71, 7632-7637.
39. Kim, M.J., Choi, Y.K., Kim, S., Kim, D., Han, K., Ko, S.B., and Park, J. (2008) Org. Lett., 10, 1295-1298.
40. Bogár, K., Vidal, P.H., Alcántara León, A.R., and Bäckvall, J.E. (2007) Org. Lett., 9, 3401-3404.
41. Träff, A., Bogár, K., Warner, M., and Bäckvall, J.E. (2008) Org. Lett., 10, 4807-4810.
42. Hilker, I., Rabani, G., Verzijl, G.K.M., Palmans, A.R.A., and Heise, A. (2006) Angew. Chem., 118, 2184-2186
43. Angew. Chem. Int. Ed., (2006), 45, 2130-2132.
44. Hilker, I., Verzijl, G.K.M., Palmans, A.R.A., and Heise, A. (2006) Polymer Preprints, 47, 222-223.
45. Berkessel, A., Sebastian-Ibarz, M.L., and Müller, T.N. (2006) Angew. Chem., 118, 6717-6720; Angew. Chem. Int. Ed., (2006), 45, 6567-6570.
46. Angew. Chem. Int. Ed., (2006), 45, 6567-6570
47. Reetz, M.T. and Schimossek, K. (1996) Chimia, 50, 668-669.
48. Paetzold, J. and Bäckvall, J.-E. (2005) J. Am. Chem. Soc., 127, 17620-17621.
49. Parvulescu, A., De Vos, D., and Jacobs, P. (2005) Chem. Commun., 5207-5309.
50. Kim, M.-J., Kim, W.-H., Han, K., Choi, Y.K., and Park, J. (2007) Org. Lett., 9, 1157-1159.
51. Choi, Y.K., Kim, M.J., and Ahn, Y. (2001) Org. Lett., 3, 4099-4101.
52. Witayakran, S., Gelbaum, L., and Ragauskas, A.J. (2007) Tetrahedron, 63, 10958-10962.
53. Denard, C.A., Huang, H., Bartlett, M.J., Lu, L., Tan, Y., Zhao, H., and Hartwig, J.F. (2013) Angew. Chem., 126, 475-479; Angew. Chem. Int. Ed., (2013), 53, 465-469.
54. Angew. Chem. Int. Ed., (2013), 53, 465-469
55. Köhler, V., Wilson, Y.M., Dürrenberger, M., Gishlieri, D., Churakova, E., Quinto, T., Knörr, L., Häussinger, D., Hollmann, F., Turner, N.J., and Ward, T.R. (2013) Nat. Chem., 5, 93-99.
56. Makkee, M., Kieboom, A.P.G., van Bekkum, H., and Roels, J.A. (1980) J. Chem. Soc., Chem. Commun., 930-931.
57. Ruddlesden, J.F. and Stewart, A. (1981) J. Chem. Res., 378-379.
58. Makkee, M., Kieboom, A.P.G., and van Bekkum, H. (1985) Carbohydr. Res., 138, 237-245.
59. Simons, C., Hanefeld, U., Arends, I.W.C.E., Maschmeyer, T., and Sheldon, R.A. (2006) Top. Catal., 40, 35-44.
60. Burda, E., Hummel, W., and Gröger, H. (2008) Angew. Chem., 120, 9693-9696
61. Angew. Chem. Int. Ed., (2008), 47, 9551-9554
62. Burda, E., Bauer, W., Hummel, W., and Gröger, H. (2010) ChemCatChem, 2, 67-72.
63. Prastaro, A., Ceci, P., Chiancone, E., Boffi, A., Cirilli, R., Colone, M., Fabrizi, G., Stringaro, A., and Cacchi, S. (2009) Green Chem., 11, 1929-1932.
64. Gauchot, V., Kroutil, W., and Schmitzer, A.R. (2010) Chem. Eur. J., 16, 6748-6751.
65. Borchert, S., Burda, E., Schatz, J., Hummel, W., and Gröger, H. (2012) J. Mol. Catal. B: Enzym., 84, 89-93.
66. Sgalla, S., Fabrizi, G., Cirilli, R., Macone, A., Bonamore, A., Boffi, A., and Cacchi, S. (2007) Tetrahedron: Asymmetry, 18, 2791-2796.
67. Boffi, A., Cacchi, S., Ceci, P., Cirilli, R., Fabrizi, G., Prastaro, A., Niembro, S., Shafir, A., and Vallribera, A. (2011) ChemCatChem, 3, 347-353.
68. Baer, K., Kraußer, M., Burda, E., Hummel, W., Berkessel, A., and Gröger, H. (2009) Angew. Chem., 121, 9519-9522
69. Angew. Chem. Int. Ed., (2009), 48, 9355-9358
70. Rulli, G., Duangdee, N., Baer, K., Hummel, W., Berkessel, A., and Gröger, H. (2011) Angew. Chem., 123, 8092-8095; Angew. Chem. Int. Ed., (2011), 50, 7944-7947.
71. Angew. Chem. Int. Ed., (2011), 50, 7944-7947
72. Sonoike, S., Itakura, T., Kitamura, M., and Aoki, S. (2012) Chem. Asian J., 7, 64-74.
73. Schnapperelle, I., Hummel, W., and Gröger, H. (2012) Chem. Eur. J., 18, 1073-1076.
74. Tenbrink, K., Seßler, M., Schatz, J., and Gröger, H. (2011) Adv. Synth. Catal., 353, 2363-2367.
75. Schoevaart, R. and Kieboom, T. (2002) Tetrahedron Lett., 43, 3399-3400.