A mesoporous-silica-immobilized oxovanadium cocatalyst for the lipase-catalyzed dynamic kinetic resolution of racemic alcohols

Angewandte Chemie - International Edition

Volumn 52, Issue 13, 2013, Pages 3654-3658

  Egi, Masahiro ^a   Sugiyama, Koji ^a   Saneto, Moriaki ^a   Hanada, Ryosuke ^a   Kato, Katsuya ^b   Akai, Shuji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

alcohols; dynamic kinetic resolution; lipases; mesoporous silica; vanadium

Indexed keywords

COCATALYST; DYNAMIC KINETIC RESOLUTION; LIPASE-CATALYZED; MESOPOROUS SILICA; OPTICAL YIELDS; OPTICALLY ACTIVE ESTERS; OXOVANADIUM; RACEMIC ALCOHOLS;

ALCOHOLS; CATALYSTS; LIPASES; SILICA; VANADIUM;

KINETICS;

ALCOHOL DERIVATIVE; ESTER; IMMOBILIZED PROTEIN; OXYGEN; SILICON DIOXIDE; TRIACYLGLYCEROL LIPASE; VANADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; KINETICS; METABOLISM; POROSITY; STEREOISOMERISM;

ALCOHOLS; CATALYSIS; ESTERS; IMMOBILIZED PROTEINS; KINETICS; LIPASE; OXYGEN; POROSITY; SILICON DIOXIDE; STEREOISOMERISM; VANADIUM;

EID: 84875336796     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208988     Document Type: Article

References (51)

1. M. Rueping, R. M. Koenigs, I. Atodiresei, Chem. Eur. J. 2010, 16, 9350
2. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999
3. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633
4. N. T. Patil, V. S. Shinde, B. Gajula, Org. Biomol. Chem. 2012, 10, 211.
5. K. Baer, M. Kraußer, E. Burda, W. Hummel, A. Berkessel, H. Gröger, Angew. Chem. 2009, 121, 9519
6. Angew. Chem. Int. Ed. 2009, 48, 9355
7. B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. 2010, 122, 858
8. Angew. Chem. Int. Ed. 2010, 49, 846
9. D. E. A. Raup, B. Cardinal-David, D. Holte, K. A. Scheidt, Nat. Chem. 2010, 2, 766
10. B. M. Trost, X. Luan, Y. Miller, J. Am. Chem. Soc. 2011, 133, 12824
11. S. Zhou, S. Fleischer, K. Junge, M. Beller, Angew. Chem. 2011, 123, 5226
12. Angew. Chem. Int. Ed. 2011, 50, 5120, and references therein.
13. A. Kamal, M. A. Azhar, T. Krishnaji, M. S. Malik, S. Azeeza, Coord. Chem. Rev. 2008, 252, 569
14. J. H. Lee, K. Han, M.-J. Kim, J. Park, Eur. J. Org. Chem. 2010, 999
15. M. C. Warner, C. P. Casey, J.-E. Bäckvall, Top. Organomet. Chem. 2011, 37, 85.
16. J.-E. Bäckvall, J. Organomet. Chem. 2002, 652, 105
17. S. Wuyts, D. E. De Vos, F. Verpoort, D. Depla, R. De Gryse, P. A. Jacobs, J. Catal. 2003, 219, 417
18. C. Roengpithya, D. A. Patterson, E. J. Gibbins, P. C. Taylor, A. G. Livingston, Ind. Eng. Chem. Res. 2006, 45, 7101
19. Y. Ahn, S.-B. Ko, M.-J. Kim, J. Park, Coord. Chem. Rev. 2008, 252, 647.
20. L. K. Thalén, A. Sumic, K. Bogár, J. Norinder, A. K. Å. Persson, J.-E. Bäckvall, J. Org. Chem. 2010, 75, 6842
21. A. Träff, R. Lihammer, J.-E. Bäckvall, J. Org. Chem. 2011, 76, 3917
22. H. Kim, Y. K. Choi, J. Lee, E. Lee, J. Park, M.-J. Kim, Angew. Chem. 2011, 123, 11136
23. Angew. Chem. Int. Ed. 2011, 50, 10944.
24. S. Akai, K. Tanimoto, Y. Kanao, M. Egi, T. Yamamoto, Y. Kita, Angew. Chem. 2006, 118, 2654
25. Angew. Chem. Int. Ed. 2006, 45, 2592
26. S. Akai, R. Hanada, N. Fujiwara, Y. Kita, M. Egi, Org. Lett. 2010, 12, 4900.
27. P. Ödman, L. A. Wessjohann, U. T. Bornscheuer, J. Org. Chem. 2005, 70, 9551
28. S. Wuyts, J. Wahlen, P. A. Jacobs, D. E. De Vos, Green Chem. 2007, 9, 1104.
29. B. Voit, Angew. Chem. 2006, 118, 4344
30. Angew. Chem. Int. Ed. 2006, 45, 4238, and references therein
31. F. Gelman, J. Blum, D. Avnir, J. Am. Chem. Soc. 2002, 124, 14460
32. R. K. Zeidan, S.-J. Hwang, M. E. Davis, Angew. Chem. 2006, 118, 6480
33. Angew. Chem. Int. Ed. 2006, 45, 6332.
34. Q.-H. Fan, Y.-M. Li, A. S. C. Chan, Chem. Rev. 2002, 102, 3385
35. A. F. Trindade, P. M. P. Gois, C. A. M. Afonso, Chem. Rev. 2009, 109, 418
36. M. J. Climent, A. Corma, S. Iborra, Chem. Rev. 2011, 111, 1072.
37. Lipase-catalyzed DKR using zeolite as a racemization catalyst has been reported, albeit using only 1-phenylethanol. This method was partly accompanied by the formation of styrene during the racemization, see:, Y. Zhu, K.-L. Fow, G.-K. Chuah, S. Jaenicke, Chem. Eur. J. 2007, 13, 541.
38. Y. Wan, D. Zhao, Chem. Rev. 2007, 107, 2821
39. N. Linares, E. Serrano, M. Rico, A. M. Balu, E. Losada, R. Luque, J. García-Martínez, Chem. Commun. 2011, 47, 9024.
40. For the good compatibility of lipases and MPS, see:, K. Kato, R. Irimescu, T. Saito, Y. Yokogawa, H. Takahashi, Biosci. Biotechnol. Biochem. 2003, 67, 203.
41. At the beginning of this project, we synthesized MPS according to a previous report, see:, K. Kato, M. Suzuki, M. Tanemura, T. Saito, J. Ceram. Soc. Jpn. 2010, 118, 410. Later, it was provided by Taiyo Kagaku Co. Ltd.
42. G. Du, S. Lim, M. Pinault, C. Wang, F. Fang, L. Pfefferle, G. L. Haller, J. Catal. 2008, 253, 74.
43. The increase in catalytic activity for the 1,3-isomerization of allylic alcohols was accompanied by the formation of biallyl ethers, see:, C. Morrill, G. L. Beutner, R. H. Grubbs, J. Org. Chem. 2006, 71, 7813.
44. H. Fujioka, S. Matsuda, M. Horai, E. Fujii, M. Morishita, N. Nishiguchi, K. Hata, Y. Kita, Chem. Eur. J. 2007, 13, 5238.
45. H. Ouchi, Y. Mihara, H. Takahata, J. Org. Chem. 2005, 70, 5207.
46. V. Cadierno, P. Crochet, S. E. García-Garrido, J. Gimeno, Dalton Trans. 2010, 39, 4015.
47. J. C. Shattuck, C. M. Shreve, S. E. Solomon, Org. Lett. 2001, 3, 3021
48. M. P. Doyle, W. Hu, M. V. Valenzuela, J. Org. Chem. 2002, 67, 2954
49. H. M. L. Davies, Q. Jin, Tetrahedron: Asymmetry 2003, 14, 941
50. J. A. Carr, K. S. Bisht, Org. Lett. 2004, 6, 3297
51. Y. Takashima, Y. Kobayashi, J. Org. Chem. 2009, 74, 5920.