Dynamic Kinetic Resolution of rac-2-Hydroxy-1-indanone by using a Heterogeneous Ru(OH)3/Al2O3 Racemization Catalyst and Lipase

ChemCatChem

Volumn 2, Issue 12, 2010, Pages 1615-1621

  Långvik, Otto ^a   Saloranta, Tiina ^a   Kirilin, Alexey ^b   Liljeblad, Arto ^c   Mäki Arvela, Päivi ^b   Kanerva, Liisa T ^c   Murzin, Dmitry Yu ^b   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b LABORATORY OF INDUSTRIAL CHEMISTRY AND REACTION ENGINEERING   (Finland)

^c UNIVERSITY OF TURKU   (Finland)

Author keywords

Dynamic kinetic resolution; Enzyme catalysis; Heterogeneous catalysis; Ruthenium; Supported catalysts

Indexed keywords

EID: 79957858832     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000161     Document Type: Article

References (57)

1. M.-J. Kim, Y. Ahn, J. Park, Curr. Opin. Biotechnol. 2002, 13, 578-587;
2. O. Pàmies, J.-E. Bäckvall, Chem. Rev. 2003, 103, 3247-3262;
3. N. J. Turner, Curr. Opin. Chem. Biol. 2004, 8, 114-119;
4. B. Martín-Matute, J.-E. Bäckvall, Curr. Opin. Chem. Biol. 2007, 11, 226-232;
5. J. H. Lee, K. Han, M.-J. Kim, J. Park, Eur. J. Org. Chem. 2010, 999-1015.
6. M. Inagaki, J. Hiratake, T. Nishioka, J. Oda, J. Org. Chem. 1992, 57, 5643-5649;
7. L. T. Kanerva, K. Rahiala, O. Sundholm, Biocatalysis 1994, 10, 169-180.
8. P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623-7626.
9. A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall Angew. Chem. Int. Ed. Engl. 1997, 36, 1211-1212;
10. A. L. E. Larsson, B. A. Persson, J.-E. Bäckvall, Angew. Chem. Int. Ed. Engl. 1997, 36, 1211-1212;
11. B. A. Persson, A. L. E. Larsson, M. LeRay, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 1645-1650.
12. Y. Ahn, S.-B. Ko, M.-J. Kim, J. Park, Coord. Chem. Rev. 2008, 252, 647-658;
13. D. Strübing, P. Krumlinde, J. Piera, J.-E. Bäckvall, Adv. Synth. Catal. 2007, 349, 1577-1581;
14. B. A. C. vanAs, J. vanBuijtenen, T. Mes, A. R. A. Palmans, E. W. Meijer, Chem. Eur. J. 2007, 13, 8325-8332;
15. J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem. 2002, 114, 2479-2482
16. J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem. Int. Ed. 2002, 41, 2373-2376.
17. A. Berkessel, M. L. Sebastian-Ibarz, T. N. Müller, Angew. Chem. 2006, 118, 6717-6720; Angew. Chem. Int. Ed. 2006, 45, 6567-6570;
18. A. Berkessel, M. L. Sebastian-Ibarz, T. N. Müller Angew. Chem. Int. Ed. 2006, 45, 6567-6570;
19. D. Klomp, K. Djanashvili, N. C. Svennum, N. Chantapariyavat, C.-S. Wong, F. Vilela, T. Maschmeyer, J. A. Peters, U. Hanefeld, Org. Biomol. Chem. 2005, 3, 483-489;
20. D. Klomp, T. Maschmeyer, U. Hanefeld, J. A. Peters, Chem. Eur. J. 2004, 10, 2088-2093.
21. P. Ödman, L. A. Wessjohan, U. T. Bornscheuer, J. Org. Chem. 2005, 70, 9551-9555;
22. S. Wuyts, K. deTemmerman, D. E. deVos, P. A. Jacobs, Chem. Eur. J. 2005, 11, 386-397;
23. Y. Zhu, K.-L. Fow, G.-K. Chuah, S. Jaenicke, Chem. Eur. J. 2007, 13, 541-547;
24. S. Wuyts, K. deTemmerman, D. E. deVos, P. Jacobs, Chem. Commun. 2003, 1928-1929;
25. S. Wuyts, J. Wahlen, P. A. Jacobs, D. E. deVos, Green Chem. 2007, 9, 1104-1108;
26. N. Ravasio, S. Riva, R. Psaro, F. Zaccheria, VIII International Symposium on Catalysis Applied to Fine Chemicals Verbania-Pallanza, Italy, September 16-20, 2007, Book of Abstracts, P38;
27. F. Zaccheria, N. Ravasio, R. Psaro, A. Fusi, Chem. Eur. J. 2006, 12, 6426-6431;
28. S. Wuyts, D. E. deVos, F. Verpoort, D. Depla, R. deGryse, P. A. Jacobs, J. Catal. 2003, 219, 417-424;
29. K. Yamaguchi, T. Koike, M. Kotani, M. Matsushita, S. Shinachi, N. Mizuno, Chem. Eur. J. 2005, 11, 6574-6582;
30. K. Yamaguchi, T. Koike, J. W. Kim, Y. Ogasawara, N. Mizuno, Chem. Eur. J. 2008, 14, 11480-11487;
31. À. Zsigmond, A. Kecskeméti, K. Bogár, F. Notheisz, E. Mernyák, Catal. Commun. 2005, 6, 520-524.
32. N. Kim, S.-B. Ko, M. S. Kwon, M.-J. Kim, J. Park, Org. Lett. 2005, 7, 4523-4526.
33. M. T. Reetz, K. Schimossek, Chimia 1996, 50, 668-669.
34. H. Kajiro, S. Mitamura, A. Mori, T. Hiyama, Bull. Chem. Soc. Jpn. 1999, 72, 1093-1100.
35. C. H. Senanayake, Aldrichimica Acta 1998, 31, 3-16;
36. A. K. Ghosh, S. Fidanze, C. H. Senanayake, Synthesis 1998, 937-961;
37. Y. Hong, Y. Gao, X. Nie, C. M. Zepp, Tetrahedron Lett. 1994, 35, 6631-6634.
38. P. Hoyos, J.-V. Sinisterra, F. Molinari, A. R. Alcántara, P. D. deMaría, Acc. Chem. Res. 2010, 43, 288-299.
39. W. Adam, M. T. Díaz, R. T. Fell, C. R. Saha-Möller, Tetrahedron: Asymmetry 1996, 7, 2207-2210.
40. Z. Cs. Gyarmati, A. Liljeblad, G. Argay, A. Kálmán, G. Bernáth, L. T. Kanerva, Adv. Synth. Catal. 2004, 346, 566-572.
41. J. L. L. Rakels, A. J. J. Straathof, J. J. Heijnen, Enzyme Microb. Technol. 1993, 15, 1051-1056;
42. C.-S. Chen, Y. Fujimoto, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
43. I. Ben-David, E. Mishani, S. Rozen, J. Org. Chem. 1998, 63, 4632-4635.
44. In the present work, the actual racemization mechanism was not studied in detail and the catalyst was assigned with the oxidation state (+III) it had before reaction.
45. A. Kirilin, P. Mäki-Arvela, M. Rupp, E. Toukonity, N. Kumar, K. Kordas, L. M. Kustov, T. Salmi, D. Yu. Murzin, Res. Chem. Intermed. 2010, 36, 193-210;
46. P. Mäki-Arvela, S. Sahin, K. Eränen, D. Yu. Murzin, Res. Chem. Intermed. 2010, 36, 245-252;
47. P. Mäki-Arvela, S. Sahin, N. Kumar, J.-P. Mikkola, K. Eränen, T. Salmi, D. Yu. Murzin, Catal. Today 2009, 140, 70-73;
48. P. Mäki-Arvela, S. Sahin, N. Kumar, T. Heikkilä, V.-P. Lehto, T. Salmi, D. Yu. Murzin, Appl. Catal. A 2008, 350, 24-29.
49. J. Pietruszka, R. C. Simon, F. Kruska, M. Braun, Eur. J. Org. Chem. 2009, 6217-6224.
50. I. Busygin, M. Rosenholm, E. Toukoniitty, D. Yu. Murzin, R. Leino, Catal. Lett. 2007, 117, 91-98.
51. R. Laatikainen, M. Niemitz, U. Weber, J. Sundelin, T. Hassinen, J. Vepsäläinen, J. Magn. Reson. Ser. A 1996, 120, 1-10;
52. For detailed information on the software, see: date of access 10.5.2010.
53. C. A. Emeis, J. Catal. 1993, 141, 347-354.
54. M. P. Cava, R. L. Litle, D. R. Napier, J. Am. Chem. Soc. 1958, 80, 2257-2263;
55. P. K. Banerjee, D. Mukhopadhyay, D. N. Chaudhury, J. Indian Chem. Soc. 1965, 42, 115-120.
56. L. T. Kanerva, O. Sundholm, J. Chem. Soc. Perkin Trans. 1 1993, 2407-2410.
57. P. Mäki-Arvela, N. Kumar, V. Nieminen, R. Sjöholm, T. Salmi, D. Yu. Murzin, J. Catal. 2004, 225, 155-169.