Resolution of a chiral alcohol through lipase-catalyzed transesterification of its mixed carbonate by poly(ethylene glycol) in organic media

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1279-1288

  Whalen, Lisa J ^a   Morrow, Cary J ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBONIC ACID; MACROGOL; ORGANIC COMPOUND; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0034616265     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00068-9     Document Type: Article

References (46)

1. Jones, J. B. Tetrahedron 1986, 42, 3351.
2. Biocatalysts in Organic Synthesis; Tramper, J.; van der Plas, H. C.; Linko, P., Eds.; Elsevier: New York, 1985.
3. Enzyme Chemistry: Impact and Applications; Suckling, C. J., Ed.; Chapman and Hall: New York, 1984.
4. Enzymatic Reactions in Organic Media; Koskinen, A. M. P.; Klibanov, A. M., Eds.; Blackie: New York, 1996.
5. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook; Drauz, K.; Waldmann, H., Eds.; VCH: New York, 1995.
6. Cambou, B.; Klibanov, A. M. J. Am. Chem. Soc. 1984, 106, 2687.
7. Zaks, A.; Klibanov, A. M. Science 1984, 224, 1249.
8. Gatfield, I. L. Ann. N.Y. Acad. Sci. 1984, 568.
9. Zaks, A.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 3192.
10. Klibanov, A. M. Chemtech 1986, 354.
11. Wilson, W. K.; Baca, S. B.; Barber, Y. J.; Scallen, T. J.; Morrow, C. J. J. Org. Chem. 1983, 48, 3960.
12. For more applications of PEG in organic synthesis, see: Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
13. Wallace, J. S.; Reda, K. B.; Williams, M. E.; Morrow, C. J. J. Org. Chem. 1990, 55, 3544.
14. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174.
15. Abramowicz, D. A.; Keese, C. R. Biotechnol. Bioeng. 1989, 33, 149.
16. Maestro, A.; Astorga, C.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3153.
17. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 10725.
18. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry 1995, 6, 2797.
19. Pozo, M.; Pulido, R.; Gotor, V. Tetrahedron 1992, 48, 6477.
20. Moris, F.; Gotor, V. J. Org. Chem. 1992, 57, 2490.
21. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 4321.
22. Kawashima, M.; Hasegawa, T. Biotechnol. Lett. 1993, 15, 465.
23. Yang, Y. L.; Ramaswamy, S. G.; Jakoby, W. B. J. Biol. Chem. 1998, 273, 7814.
24. (a) Matsumoto, K.; Fuwa, S.; Kitajima, H. Tetrahedron Lett. 1995, 36, 6499.
25. (b) Matsumoto, K.; Fuwa, S.; Shimojo, M.; Kitajima, H.; Hatanaka, M. Synlett 1996, 11, 1085.
26. Matsumoto, K.; Shimojo, M.; Hatanaka, M. Chem. Lett. 1997, 11, 1151.
27. Matsumoto, K.; Fuwa, S.; Shimojo, M.; Kitajima, H. Bull. Chem. Soc. Jpn. 1996, 69, 2977.
28. See: Ref. 4, pp. 194-195.
29. Kanerva, L. T.; Sundholm, O. J. Chem. Soc., Perkin Trans. 1 1993, 1385.
30. Gou, D.-M.; Liu, Y.-C.; Chen, C. S. J. Org. Chem. 1993, 58, 1287.
31. Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635.
32. Preparative Biotransformations; Roberts, S. M.; Casy, G., Eds.; John Wiley & Sons: Chichester, 1994.
33. Bianchi, D.; Cabri, W.; Cesti, P.; Francacalanci, F.; Ricci, M. J. Org. Chem. 1988, 53, 104.
34. Mohr, P.; Rosslein, L.; Tamm, C. Tetrahedron Lett. 1989, 30, 2513.
35. Ramaswamy, S.; Hui, R. A. F.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1986, 1545.
36. Burgess, K.; Henderson, I. Tetrahedron Lett. 1989, 30, 3633.
37. Guibe-Jampel, E.; Rousseau, G.; Salaun, J. J. Chem. Soc., Chem. Commun. 1987, 1080.
38. Salaun, J.; Karkour, B. Tetrahedron Lett. 1987, 28, 4669.
39. Barnier, J. P.; Blanco, L.; Guibe-Jampel, E.; Rousseau, G. Tetrahedron 1989, 45, 5051.
40. Knezovic, S.; Sunjic, V. Tetrahedron: Asymmetry 1993, 4, 313.
41. Blanco, L.; Rousseau, G.; Barnier, J. P.; Guibe-Jampel, E. Tetrahedron: Asymmetry 1993, 4, 783.
42. Boaz, N. W. J. Org. Chem. 1992, 57, 4289.
43. Brazwell, G. Ph.D. Dissertation, University of New Mexico, 1992.
44. Goering, H.; Eikenberry, J.; Koermer, G.; Lattimer, C. J. Am. Chem. Soc. 1974, 96, 1493.
45. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th ed.; Budavari, S., Ed.; Merck & Co., Inc.: Rahway, NJ, 1989; p. 820.
46. Ohta, S.; Yamashita, M.; Nagai, N.; Kawasaki, I.; Maeda, K.; Miyano, Y. Heterocycles 1995, 41, 1683.