Core-Shell Composite as the Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols

ChemCatChem

Volumn 5, Issue 1, 2013, Pages 247-254

  Wang, Jie ^a   Do, Dong Minh ^a   Chuah, Gaik Khuan ^a   Jaenicke, Stephan ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Alcohols; Enantioselectivity; Enzyme catalysis; Heterogeneous catalysis; Transesterification

Indexed keywords

1-PHENYLETHANOL; ACIDIC SITES; ACYL DONORS; BETA ZEOLITE; CONTROLLABLE SHELL THICKNESS; CORE-SHELL; CORE-SHELL COMPOSITES; DYNAMIC KINETIC RESOLUTION; ENANTIOPURITY; ENZYME CATALYSIS; ESTER FORMATION; LIPASE-CATALYZED; MICRO-COMPOSITES; ONE POT; SECONDARY ALCOHOLS; SIDE PRODUCTS; SILICALITE-1 SHELL;

ALCOHOLS; CATALYSIS; DEHYDRATION; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; ETHANOL; LIPASES; SHELLS (STRUCTURES); SILICATE MINERALS; TRANSESTERIFICATION; VOLATILE FATTY ACIDS;

CATALYST SELECTIVITY;

EID: 84871658903     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200566     Document Type: Article

References (57)

1. D. Seebach, Angew. Chem. 1990, 102, 1363-1409; Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367;
2. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem. 2004, 116, 806-843; Angew. Chem. Int. Ed. 2004, 43, 788-824.
3. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938;
4. R. Noyori, T. Ohkuma, Pure Appl. Chem. 1999, 71, 1493-1501;
5. R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40-75; Angew. Chem. Int. Ed. 2001, 40, 40-73;
6. S. Roy, V. Alexandre, M. Neuwels, L. LeTexier, Adv. Synth. Catal. 2001, 343, 738-743;
7. J. Tao, A. Pettman, A. Liese, Industrial Biotransformations (Eds.: A. Liese, K. Seelbach, C. Wandrey), Wiley-VCH, Weinheim, 2006, pp.65.
8. R. Noyori, Angew. Chem. 2002, 114, 2108-2123; Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
9. M. Ikunaka, Chem. Eur. J. 2003, 9, 378-388.
10. M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. 2006, 118, 4850-4881; Angew. Chem. Int. Ed. 2006, 45, 4732-4762.
11. R. Noyori, T. Ikeda, T. Ohkuma, M. Widhalm, M. Kitamura, H. Takaya, S. Akutagawa, N. Sayo, T. Saito, J. Am. Chem. Soc. 1989, 111, 9134-9135;
12. M. Kitamura, M. Tokunaga, R. Noyori, J. Am. Chem. Soc. 1993, 115, 144-152.
13. H. Pellissier, Tetrahedron 2003, 59, 8291-8327;
14. H. Pellissier, Tetrahedron 2008, 64, 1563-1601.
15. P. Dinh, J. Howarth, A. Hudnott, J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623-7626;
16. J. Koh, H. Jung, M. Kim, J. Park, Tetrahedron Lett. 1999, 40, 6281-6284;
17. O. Pàmies, J. Bäckvall, J. Org. Chem. 2001, 66, 4022-4025;
18. O. Pàmies, J. Bäckvall, Chem-Eur. J. 2001, 7, 5052-5058;
19. T. Riermeier, P. Gross, A. Monsees, M. Hoff, H. Trauthwein, Tetrahedron Lett. 2005, 46, 3403-3406;
20. S. Akai, K. Tanimoto, Y. Kanao, M. Egi, T. Yamamoto, Y. Kita, Angew. Chem. 2006, 118, 2654-2657; Angew. Chem. Int. Ed. 2006, 45, 2592-2595;
21. B. Martin-Matute, J. Bäckvall, Curr. Opin. Chem. Biol. 2007, 11, 226-232;
22. K. Benaissi, M. Poliakoff, N. R. Thomas, Green Chem. 2009, 11, 617-621;
23. J. H. Lee, K. Han, M. Kim, J. Park, Eur. J. Org. Chem. 2010, 999-1015.
24. S. Wuyts, D. DeVos, F. Verpoort, D. Depla, R. DeGryse, P. Jacobs, J. Catal. 2003, 219, 417-424;
25. A. Zsigmond, A. Kecskemeti, K. Bogar, F. Notheisz, E. Mernyak, Catal. Commun. 2005, 6, 520-524;
26. O. Långvik, T. Saloranta, A. Kirilin, A. Liljeblad, P. Mäki-Arvela, L. T. Kanerva, D. Y. Murzin, R. Leino, ChemCatChem 2010, 2, 1615-1621.
27. S. Wuyts, K. DeTemmerman, D. DeVos, P. Jacobs, Chem. Commun. 2003, 1928-1929;
28. S. Wuyts, K. DeTemmerman, D. E. DeVos, P. A. Jacobs, Chem. Eur. J. 2005, 11, 386-397;
29. Y. Z. Zhu, K. L. Fow, G. K. Chuah, S. Jaenicke, Chem. Eur. J. 2007, 13, 541-547;
30. L. F. A. Costa, F. Lemos, F. R. Ribeiro, J. M. S. Cabral, Catal. Today 2008, 133, 625-631;
31. L. Costa, A. Coelho, F. Lemos, F. R. Ribeiro, J. M. S. Cabral, Appl. Catal. A 2009, 354, 33-37;
32. A. Fois, A. Yap, A. Masters, T. Maschmeyer, Top. Catal. 2008, 48, 153-157;
33. P. Lozano, T. DeDiego, C. Mira, K. Montague, M. Vaultier, J. L. Iborra, Green Chem. 2009, 11, 538-542;
34. X. Li, Y. Shi, Z. J. Wang, Y. H. Zhang, Y. Tang, J. Catal. 2012, 288, 24-32.
35. Y. M. Cheng, G. Xu, J. P. Wu, C. S. Zhang, L. R. Yang, Tetrahedron Lett. 2010, 51, 2366-2369.
36. D. Klomp, T. Maschmeyer, U. Hanefeld, J. A. Peters, Chem. Eur. J. 2004, 10, 2088-2093.
37. S. Wuyts, J. Wahlen, P. A. Jacobs, D. E. DeVos, Green Chem. 2007, 9, 1104-1108.
38. Y. Bouizi, I. Diaz, L. Rouleau, V. P. Valtchev, Adv. Funct. Mater. 2005, 15, 1955-1960;
39. Y. Bouizi, L. Rouleau, V. P. Valtchev, Chem. Mater. 2006, 18, 4959-4966;
40. Y. Bouizi, G. Majano, S. Mintova, V. Valtchev, J. Phys. Chem. C 2007, 111, 4535-4542;
41. M. Miyamoto, T. Kamei, N. Nishiyama, Y. Egashira, K. Ueyama, Adv. Mater. 2005, 17, 1985-1988;
42. Q. Li, Z. Wang, J. Hedlund, D. Creaser, H. Zhang, X. Zou, A. J. Bons, Microporous Mesoporous Mater. 2005, 78, 1-10;
43. D. VanVu, M. Miyamoto, N. Nishiyama, Y. Egashira, K. Ueyama, J. Catal. 2006, 243, 389-394;
44. D. Mores, E. Stavitski, S. P. Verkleij, A. Lombard, A. Cabiac, L. Rouleau, J. Patarin, A. Simon-Masseron, B. M. Weckhuysen, Phys. Chem. Chem. Phys. 2011, 13, 15985-15994;
45. X. F. Qian, J. M. Du, B. Li, M. Si, Y. S. Yang, Y. Y. Hu, G. X. Niu, Y. H. Zhang, H. L. Xu, B. Tu, Y. Tang, D. Y. Zhao, Chem. Sci. 2011, 2, 2006-2016;
46. X. F. Qian, B. Li, Y. Y. Hu, G. X. Niu, Y. H. Zhang, R. C. Che, Y. Tang, D. S. Su, A. M. Asiri, D. Y. Zhao, Chem. Eur. J. 2012, 18, 931-939.
47. C. Baerlocher, L. B. McCusker, D. H. Olson, Atlas of Zeolite Framework Types, Elsevier, Amsterdam, 2007.
48. The molecular sizes of 1-phenylethanol and 1-phenylethyl acetate were estimated using Chem3D Ultra software (FigureS1).
49. A. Corma, V. Fornes, L. Forni, F. Marquez, J. Martinez-Triguero, D. Moscotti, J. Catal. 1998, 179, 451-458;
50. S. Zheng, A. Jentys, J. A. Lercher, J. Catal. 2003, 219, 310-319;
51. K. Na, M. Choi, W. Park, Y. Sakamoto, O. Terasaki, R. Ryoo, J. Am. Chem. Soc. 2010, 132, 4169-4177;
52. Z. Musilova-Pavlackova, S. I. Zones, J. Cejka, Top. Catal. 2010, 53, 273-282;
53. J. Wang, W. M. Hua, Y. H. Yue, Z. Gao, Bioresour. Technol. 2010, 101, 7224-7230;
54. Y. J. Ji, B. Zhang, L. Xu, H. Wu, H. Peng, L. Chen, Y. Liu, P. Wu, J. Catal. 2011, 283, 168-177.
55. V. V. Ordomsky, V. Y. Murzin, Y. V. Monakhova, Y. V. Zubavichus, E. E. Knyazeva, N. S. Nesterenko, I. I. Ivanova, Microporous Mesoporous Mater. 2007, 105, 101-110;
56. V. Shetti, J. Kim, R. Srivastava, M. Choi, R. Ryoo, J. Catal. 2008, 254, 296-303.
57. For extended one-pot DKR reaction, to minimize evaporation of isopropenyl acetate (bp 92-94°C) over time, 2mmol isopropenyl acetate was added as follows: 1mmol initially, 0.5mmol after 1h and 0.5mmol at 20h.