Enzyme-Catalyzed Enantioselective Hydrolysis of 6-Membered Cyclic Carbonates Using Water-Immiscible Co-Solvent System

Synlett

Volumn 1996, Issue 11, 1996, Pages 1085-1086

  Matsumoto, Kazutsugu ^a   Shimojo, Megumi ^a   Kitajima, Hidehiko ^a   Hatanaka, Minoru ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002635048     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5696     Document Type: Article

References (25)

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2. For representative examples, see: (a) Oishi, T; Hirama, M. J. Org. Chem., 1989, 54, 5834. (b) Corey, E. J.; DaSilva Jardine, P.; Virgin, S.; Yuen, P. -W.; Connell, R. D. J. Am. Chem. Soc., 1989, 111, 9243. (c) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem., 1992, 57, 2768.
3. For representative examples, see: (a) Oishi, T; Hirama, M. J. Org. Chem., 1989, 54, 5834. (b) Corey, E. J.; DaSilva Jardine, P.; Virgin, S.; Yuen, P. -W.; Connell, R. D. J. Am. Chem. Soc., 1989, 111, 9243. (c) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem., 1992, 57, 2768.
4. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
5. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
6. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
7. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
8. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
9. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
10. Reviews for chemical methods, see; (a) Noyori, R. Chem. Soc. Rev., 1989, 18, 187. (b) Noyori, R.; Kitamura, M. Modern Synthetic Methods, 1989, 5, 115. Representative examples of enzymatic methods, see: (c) Lee, L. G.; Whiteside, G. M. J. Org. Chem., 1986, 51, 25. (d) Sato, T.; Okumura, Y.; Itai, J.; Fujisawa, T. Chem. Lett., 1988, 1537. (e) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1, 1990, 2469. (f) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron, 1991, 47, 1145. (g) Ishihara, K.; Higashi, Y.; Tsuboi, S.; Utaka, M. Chem. Lett., 1995, 253.
11. For recent examples, see: (a) Herradón, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron : Asymmetry, 1993, 4, 845. (b) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry, 1993, 4, 925. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289. (d) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem., 1994, 59, 388. (e) Fernández, S.; Ferrero, F.; Gotor, V.; Okamura, W. H. J. Org. Chem., 1995, 60.
12. For recent examples, see: (a) Herradón, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron : Asymmetry, 1993, 4, 845. (b) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry, 1993, 4, 925. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289. (d) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem., 1994, 59, 388. (e) Fernández, S.; Ferrero, F.; Gotor, V.; Okamura, W. H. J. Org. Chem., 1995, 60.
13. For recent examples, see: (a) Herradón, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron : Asymmetry, 1993, 4, 845. (b) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry, 1993, 4, 925. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289. (d) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem., 1994, 59, 388. (e) Fernández, S.; Ferrero, F.; Gotor, V.; Okamura, W. H. J. Org. Chem., 1995, 60.
14. For recent examples, see: (a) Herradón, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron : Asymmetry, 1993, 4, 845. (b) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry, 1993, 4, 925. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289. (d) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem., 1994, 59, 388. (e) Fernández, S.; Ferrero, F.; Gotor, V.; Okamura, W. H. J. Org. Chem., 1995, 60.
15. For recent examples, see: (a) Herradón, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron : Asymmetry, 1993, 4, 845. (b) Mattson, A.; Öhrner, N.; Hult, K.; Norin, T. Tetrahedron: Asymmetry, 1993, 4, 925. (c) Nagai, H.; Morimoto, T.; Achiwa, K. Synlett, 1994, 289. (d) Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. J. Org. Chem., 1994, 59, 388. (e) Fernández, S.; Ferrero, F.; Gotor, V.; Okamura, W. H. J. Org. Chem., 1995, 60.
16. (a) Matsumoto, K.; Fuwa, S.; Kitajima, H. Tetrahedron Lett., 1995, 36, 6499.
17. (b) Matsumoto, K.; Fuwa, S.; Shimojo, M.; Kitajima, H. Bull. Chem. Soc. Jpn., 1996, in press.
18. Chen, C. -S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc., 1982, 104, 7294.
19. D -4.78° (c 1.03, MeOH)) derived from L-malic acid. See, ref 4b.
20. The ee of 1 was determined by HPLC analysis with CHIRALCEL OJ (Daicel Chemical Industries, Ltd); Eluent, hexane / 2-propanol = 70 / 30; flow rate, 0.5 ml / min; retention time, 43 (S) and 48 (R) min.
21. The ee of 2 was determined by HPLC analysis of the corresponding bis-MTPA ester with Zorbax SIL (Du Pont Instruments); Eluent, hexane / AcOEt = 90 / 10; flow rate, 0.5 ml / min; retention time, 44 (S) and 49 (R) min.
22. 2O and purified using flash column chromatography on silica gel (eluent, hexane / AcOEt = 3 / 1 → AcOEt) to afford (S)-1 (33.6 mg, 36%, 77% ee) and (S)-2 (35.2 mg, 42%, 64% ee).
23. 4
24. For reviews, see: (a) Homma, J.; Kanegasaki, S.; Luderitz, O.; Shibata, T.; Westphal, O. Bacterial Endotoxin: Chemical, Biological and Clinical Aspects; Verlag Chemie; Basel, 1984. (b) Raetz, C. Annu. Rev. Biochem. 1990, 59, 129.
25. For reviews, see: (a) Homma, J.; Kanegasaki, S.; Luderitz, O.; Shibata, T.; Westphal, O. Bacterial Endotoxin: Chemical, Biological and Clinical Aspects; Verlag Chemie; Basel, 1984. (b) Raetz, C. Annu. Rev. Biochem. 1990, 59, 129.