Chemoenzymatic synthesis of enantiomerically pure 1,2-diols employing immobilized lipase in the ionic liquid [bmim]PF 6

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8801-8805

  Kamal, Ahmed ^a   Chouhan, Gagan ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME IMMOBILIZATION; ENZYME SYNTHESIS; KINETICS; LIQUID;

BURKHOLDERIA CEPACIA; PSEUDOMONAS;

EID: 7544236958     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.015     Document Type: Article

References (62)

1. S. Parida, and J.S. Dordick J. Am. Chem. Soc. 113 1991 2253 2259
2. W.L. Nelson, J.E. Wennerstrom, and S.R. Sankar J. Org. Chem. 42 1977 1006 1012
3. D. Bianchi, A. Bosetti, P. Cesti, and P. Golini Tetrahedron Lett. 33 1992 3231 3234
4. Z.-M. Wang, X.-L. Zhang, and K.B. Sharpless Tetrahedron Lett. 34 1993 2267 2270
5. J.D. White, M.-C. Kang, and B.G. Sheldon Tetrahedron Lett. 24 1983 4539 4542
6. K. Mikami, M. Terada, and T. Nakai J. Am. Chem. Soc. 112 1990 3949 3954
7. E.J. Corey, and R.K. Bakshi Tetrahedron Lett. 31 1990 611 614
8. H. Kikuchi, and K. Mori Agric. Biol. Chem. 53 1989 2095 2100
9. H.C. Brown, G.G. Pai, and P.K. Jadhav J. Am. Chem. Soc. 106 1984 1531 1533
10. K. Laumen, D. Breitgoff, R. Seemayer, and M.P. Schneider J. Chem. Soc., Chem. Commun. 1989 148 150
11. R.L. Pederson, K.K.-C. Liu, J.F. Rutan, L. Chen, and C.-H. Wong J. Org. Chem. 55 1990 4897 4901
12. C.-S. Chen, Y.-C. Liu, and M. Marsella J. Chem. Soc., Perkin Trans. 1990 2559 2561
13. U. Goergens, and M.P. Schneider J. Am. Chem. Soc., Chem. Commun. 1991 1064 1066
14. U. Goergens, and M.P. Schneider J. Chem. Soc., Chem. Commun. 1991 1066 1068
15. M.-J. Kim, and Y.K. Choi J. Org. Chem. 57 1992 1605 1607
16. P. Cesti, A. Zaks, and A.M. Klibanov Appl. Biochem. Biotechnol. 11 1985 401 407
17. A.J.M. Janssen, A.J.H. Klunder, and B. Zwanenburg Tetrahedron 47 1991 7409 7416
18. A. Bosetti, D. Bianchi, P. Cesti, P. Golini, and S. Spezia J. Chem. Soc., Perkin Trans. 1 1992 239 242
19. K. Lemke, F. Theil, A. Kunath, and H. Schick Tetrahedron: Asymmetry 7 1996 971 974
20. F. Theil, J. Weidener, S. Ballschuh, A. Kunath, and H. Schick J. Org. Chem. 59 1994 388 393
21. P. Virsu, A. Liljebland, A. Kanerva, and L.T. Kanerva Tetrahedron: Asymmetry 12 2001 2447 2455
22. For reviews see: J.D. Holbrey, and K.R. Seddon Clean. Prod. Process 1 1999 223 236
23. T. Welton Chem. Rev. 99 1999 2071 2084
24. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
25. R. Sheldon Chem. Commun. 2001 2399 2407
26. H. Bourbigou-Olivier, and L. Magna J. Mol. Catal. A 182-183 2002 419 437
27. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
28. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
29. Rogers R.D. Seddon K.R. Ionic Liquids as Green Solvents: Progress and Prospects ASC Symp. Ser. 856 2003 ACS Washington
30. J.H. Davis Jr., and P.A. Fox Chem. Commun. 2003 1209
31. C.E. Song Chem. Commun. 2004 1033 1043
32. S. Park, and R.J. Kazlauskas Curr. Opin. Biotechnol. 14 2003 432 437
33. F.V. Rantwijk, R.M. Lau, and R.A. Sheldon Trends Biotechnol. 21 2003 131 138
34. U. Kragl, M. Eckstein, and N. Kaftzik Curr. Opin. Biotechnol. 13 2002 565 571
35. R.A. Sheldon, R.M. Lau, M.J. Sorgedrager, F.V. Rantwijk, and K.R. Seddon Green Chem. 4 2002 147 151
36. J.L. Karr, A.M. Jesionowski, J.A. Berberich, R. Moulton, and A.J. Russell J. Am. Chem. Soc. 125 2003 4125 4131
37. C.E. Song Chem. Commun. 2004 1033 1043
38. P. Lozano, T. de Diego, D. Carrie, M. Vaultier, and J.L. Iborra Chem. Commun. 2002 692 693
39. M.T. Reetz, W. Wiesenhofer, G. Francio, and W. Leitner Chem. Commun. 2002 992 993
40. K.J. Lee, and M.-J. Kim J. Org. Chem. 67 2002 6845 6847
41. M. Erbeldinger, A.J. Mesiano, and A. Russell Biotechnol. Prog. 16 2000 1129 1131
42. R.M. Lau, F.V. Rantwijk, K.R. Seddon, and R.A. Sheldon Org. Lett. 2 2001 4189 4191
43. K.-W. Kim, B. Song, M.-Y. Choi, and M.-J. Kim Org. Lett. 3 2001 1507 1509
44. T. Itoh, E. Akasaki, K. Kudo, and S. Shirakami Chem. Lett. 2001 262 263
45. S.H. Schöfer, N. Kaftzik, P. Wasserscheid, and U. Kragl Chem. Commun. 2001 425 426
46. S. Park, and R.J. Kazlauskas J. Org. Chem. 66 2001 8395 8401
47. W. Pei, S. Li, X. Nie, Y. Li, J. Pei, B. Chen, J. Wu, and X. Ye Synthesis 1998 1298 1304
48. H. Sakuragi, T. Koyama, M. Sakurazawa, N. Yasui, K. Tokumaru, and K. Ueno Bull. Chem. Soc. Jpn. 67 1994 1769 1772
49. J.M. Miller, I.D. Brindel, S.R. Cater, K.-H. So, and J.H. Clark Anal. Chem. 52 1980 2430 2432
50. J.I. DeGraw Tetrahedron 28 1972 967 972
51. R.H. Levin, B.J. Magerlin Jr., A.V. McIntosh, A.R. Hanze, G.S. Fonken, J.L. Thompson, A.M. Searcy, M.A. Scheri, and E.S. Gutsell J. Am. Chem. Soc. 76 1954 546 547
52. 2 was removed in vacuo to afford the ionic liquid, which could be recycled in subsequent runs
53. A. Kamal, Y. Damayanthi, B.S.N. Reddy, B. Laxminarayana, and B.S.P. Reddy Chem. Commun. 1997 1015 1016
54. A. Kamal, K.V. Ramana, and M.V. Rao J. Org. Chem. 66 2001 997 1001
55. A. Kamal, G.B.R. Khanna, R. Ramu, and T. Krishnaji Tetrahedron Lett. 44 2003 4783 4787
56. A. Kamal, A.A. Shaik, M. Sandbhor, and M.S. Malik Tetrahedron: Asymmetry 15 2004 935 939
57. P. Moussou, A. Archelas, J. Baratti, and R. Furstoss J. Org. Chem. 63 1998 3532 3537
58. C.A.G.M. Weijers Tetrahedron: Asymmetry 8 1997 639 647
59. T. Tsujigami, T. Sugai, and H. Ohta Tetrahedron: Asymmetry 12 2001 2543 2549
60. 6 (0.5 mL) was added vinyl acetate (6 equiv) and lipase PS-C (0.5 equiv w/w) at room temperature. The mixture was stirred at room temperature for the appropriate time (see Table 3). After about 50% conversion of the reaction as indicated by HPLC/TLC, ether (3 × 3 mL) was added to the reaction mixture with stirring for 5 min.
61. 4 and evaporated to give the 1,2-diols.
62. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Shi J. Am. Chem. Soc. 104 1982 7294 7299