Lipase promoted asymmetric trans-esterification of 4-alkyl-,3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 2001, Pages 71-77

  Sakai, Naoko ^a   Ageishi, Satoru ^a   Isobe, Hiroshi ^a   Hayashi, Yoshiyuki ^a   Yamamoto, Yukio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

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EID: 52549129426     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. Review: A. Pommier and J. M. Pons, Synthesis, 1993, 41.
2. S. Hanessian, A. Tehim and P. Chen, J. Org. Chem., 1993, 58, 7768 and references cited therein.
3. Review: H. M. Müller and D. Seebach, Angew. Chem., Int. Ed. Engl., 1993, 32, 477;
4. review: I. Collins, J. Chem. Soc., Perkin Trans. 1, 1999, 1377.
5. J. E. Kemnitzer, S. P. McCarthy and R. A. Gross, Macromolecules, 1993, 26, 6143 and references cited therein;
6. J. E. Kemnitzer, S. P. McCarthy and R. A. Gross, Macromolecules, 1993, 26, 1221;
7. Y. Hori, M. Suzuki, A. Yamaguchi and T. Nishishita, Macromolecules, 1993, 26, 5533.
8. A. Griesbeck and D. Seebach, Helv. Chem. Acta, 1987, 70, 1320;
9. S. Cammas, I. Renard, K. Boutault and P. Guèrin, Tetrahedron: Asymmetry, 1993, 4, 1925;
10. G. Capozzi, S. Roelens and S. Talami, J. Org. Chem., 1993, 58, 7932.
11. T. Ohta, T. Miyake and H. Takaya, J. Chem. Soc., Chem. Commun., 1992, 1725;
12. T. Ohta, T. Miyake, N. Seido, H. Kumobayashi and H. Takaya, J. Org. Chem., 1995, 60, 357.
13. H. Wynberg and E. G. J. Staring, J. Am. Chem. Soc., 1982, 104, 166;
14. P. E. F. Ketelaar, E. G. J. Starling and H. Wynberg, Tetrahedron Lett., 1985, 26, 4665.
15. Y. Tamai, H. Yoshiwara, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Chem. Commun., 1994, 2281;
16. Y. Tamai, M. Someya, J. Fukumoto and S. Miyano, J. Chem. Soc., Perkin Trans. 1, 1994, 1549.
17. (a) B. W. Dymock, P. J. Kocienski, J.-M. Pons, Synthesis, 1998, 1655;
18. (b) An asymmetric synthesis of oxetan-2-ones of high ee's was reported very recently: S. G. Nelson, T. J. Peelen and Z. Wan, J. Am. Chem. Soc., 1999, 121, 9742.
19. Reviews: W. Boland, C. Fröl and M. Lorenz, Synthesis, 1991, 1049;
20. K. Faber and S. Riva, Synthesis, 1992, 895;
21. E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071;
22. J. Otera, Chem. Rev., 1993, 93, 1449.
23. E. Fouque and G. Rousseau, Synthesis, 1989, 661;
24. L. Blanco, E. Guibé-Jampel and G. Rousseau, Tetrahedron Lett., 1988, 29, 1915;
25. E. Guibé-Jampel, G. Rousseau and L. Blanco, Tetrahedron Lett., 1989, 30, 67.
26. H. Yamada, T. Sugai, H. Ohta and S. Yoshikawa, Agric. Biol. Chem., 1990, 54, 1579;
27. H. Yamada, S. Ohsawa, T. Sugai, H. Ohta and S. Yoshikawa, Chem. Lett., 1989, 1775;
28. E. Fukusaki, S. Senda, Y. Nakazono and T. Omata, Tetrahedron, 1991, 47, 6223;
29. A. L. Gutman and T. Bravdo, J. Org. Chem., 1989, 54, 4263.
30. K. Suginaka, Y. Hayashi and Y. Yukio, Tetrahedron: Asymmetry, 1996, 7, 1153;
31. N. Öhner, M. Martinelle, A. Mattson, T. Norin and K. Hult, Biotechnol. Lett., 1992, 14, 263.
32. Y. Koichi, K. Suginaka and Y. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 1995, 1645.
33. W. Adam, P. Groer, C. R. Saha-Möller, Tetrahedron: Asymmetry, 1997, 8, 833.
34. T. Ito, M. Shimizu and T. Fujisawa, Tetrahedron, 1998, 54, 5523.
35. J. R. Clemens, Chem. Rev., 1986, 86, 241.
36. L. Brikofer, A. Ritter and J. Schramn, Chem. Ber., 1962, 95, 426.
37. C. H. Heathcock, M. C. Pirrung, S. H. Montgomery and J. Lampe, Tetrahedron, 1981, 37, 4087.
38. D. A. Evans, J. Bartroli and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127.
39. W. Adam, J. Baeza and J. Liu, J. Am. Chem. Soc., 1972, 22, 2000.
40. S. E. Ramer, R. N. Moore and J. C. Vederas, Can. J. Chem., 1986, 64, 706.
41. S. C. Chen, Y. Fujimoto, G. Girdaukas and J. C. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
42. J. L. L. Rakels, A. J. J. Straathof and J. J. Heijnen, Enzyme Microb. Technol., 1993, 15, 1051.
43. P. Hadváry, H. Lengsfeld and H. Wolfer, Biochem. J., 1988, 256, 357;
44. B. Borgström, Biochem. Biophys. Acta, 1988, 962, 308;
45. reviews: R. D. Schmid and R. Verger, Angew. Chem., Int. Ed., 1998, 37, 1608.
46. F. D. Taber, B. P. Deker and J. L. Silverberg, J. Org. Chem., 1992, 57, 5990.
47. A. Tai, T. Harada, Y. Hiraki and S. Murakami, Bull. Chem. Soc. Jpn., 1983, 56, 1414.
48. M. Utaka, H. Watabu, H. Higashi, T. Sakai, S. Tsuboi and S. Torii, J. Org. Chem., 1990, 55, 3917.
49. M. Nakahata, M. Imaida, H. Ozaki, T. Harada and A. Tai, Bull. Chem. Soc. Jpn., 1982, 55, 2186.
50. M. Hamamouchi and R. E. Prud'homme, J. Polym. Sci., Polym. Chem. Ed., 1988, 26, 1593.
51. M. Sprecher, J. Biol. Chem., 1966, 241, 868.