Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem-Dihalocyclopropane Derivatives

Advanced Synthesis and Catalysis

Volumn 345, Issue 6-7, 2003, Pages 695-698

  Wang, Mei Xiang ^a   Feng, Guo Qiang ^a   Zheng, Qi Yu ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

2,2 dihalo 3 phenylcyclopropanecarboxylic acid derivatives; Amidase; Biotransformation; Enantioselectivity; Hydrolysis; Kinetic resolution; Nitrile hydratase; Rhodococcus sp. AJ270

Indexed keywords

2,2 DICHLORO 3 PHENYLCYCLOPROPANECARBOXYLIC ACID; AMIDE; BACTERIAL ENZYME; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; NITRILE; NITRILE HYDRATASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; BIOTRANSFORMATION; CYCLOPROPANATION; DEHALOGENATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NONHUMAN; REACTION ANALYSIS; RHODOCOCCUS; SYNTHESIS;

EID: 0242691663     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303020     Document Type: Article

References (37)

1. Y. Nishii, Y. Tanabe, Tetrahedron Lett. 1995, 36, 8803.
2. Y. Tanabe, K. Wakimura, Y. Nishii, Y. Muroya, Synthesis 1996, 388.
3. S. Seko, Y. Tanabe, G. Suzukamo, Tetrahedron Lett. 1990, 31, 6883.
4. M. Suda, Tetrahedron Lett. 1980, 21, 4355.
5. C. Santelli-Rouvier, Tetrahedron 1981, 37, 4195.
6. K. H. Holm, L. Skattebol, Tetrahedron Lett. 1977, 2347.
7. K. H. Holm, E. A. Mohamed, L. Skattebol, Acta Chem. Scand. 1993, 47, 500.
8. Y. Kobayashi, T. Taguchi, T. Morikawa, T. Takase, H. Takanashi, J. Org. Chem. 1982, 47, 3232.
9. Y. Nishii, H. Matsumura, Y. Muroya, T. Tsuchiya, Y. Tanabe, Biosci. Biotech. Biochem. 1995, 59, 1355.
10. Y. Tanabe, Y. Nishii, K. Wakimura, Chem. Lett. 1994, 1757.
11. T. Harada, T. Katsuhira, K. Hattori, A. Oku, J. Org. Chem. 1993, 58, 2958.
12. A. Shibuya, A. Sato, T. Taguchi, Bioorg. Med. Chem. Lett. 1998, 8, 1979.
13. K. Miyazawa, D. S. Yufit, J. A. K. Howard, A. Meijere, Eur. J. Org. Chem. 2000, 4109.
14. T. Itoh, K. Mitsukura, M. Furutani, Chem. Lett. 1998, 903.
15. K. Mitsukura, S. Korekiyo, Y. Itoh, Tetrahedron Lett. 1999, 40, 5739.
16. For recent reviews, see: a) T. Sugai, T. Yamazaki, M. Yokoyama, H. Ohta, Biosci. Biotech. Biochem. 1997, 61, 1419; b) J. Crosby, J. Moiliet, J. S. Parratt, N. J. Turner, J. Chem. Soc. Perkin Trans. 1 1994, 1679.
17. For recent reviews, see: a) T. Sugai, T. Yamazaki, M. Yokoyama, H. Ohta, Biosci. Biotech. Biochem. 1997, 61, 1419; b) J. Crosby, J. Moiliet, J. S. Parratt, N. J. Turner, J. Chem. Soc. Perkin Trans. 1 1994, 1679.
18. a) D. B. Harper, Biochem. Soc. Trans. 1976, 4, 502;
19. b) D. B. Harper, Biochem. J. 1977, 165, 309;
20. c) M. Kobayashi, S. Shimizu, FEMS Microbiol. Lett. 1994, 120, 217.
21. a) Y. Asano, Y. Tani, H. Yamada, Agric. Biol. Chem. 1980, 44, 2251;
22. b) Y. Asano, K. Fujishiro, Y. Tani, H. Yamada, Agric. Biol. Chem. 1982, 46, 1165;
23. c) Y. Asano, M. Tachibana, Y. Tani, H. Yamada, Agric. Biol. Chem. 1982, 46, 1175.
24. A. J. Blakey, J. Colby, E. Williams, C. O'Reilly, FEMS Microbiology Lett. 1995, 129, 57.
25. a) O. Meth-Cohn, M.-X. Wang, Tetrahedron Lett. 1995, 36, 9561;
26. b) O. Meth-Cohn, M.-X. Wang, J. Chem. Soc. Perkin Trans. 1 1997, 1099.
27. a) O. Meth-Cohn, M.-X. Wang, Chem. Commun. 1997, 1041;
28. b) O. Meth-Cohn, M.-X. Wang, J. Chem. Soc. Perkin Trans. 1 1997, 3197.
29. a) M.-X. Wang, G. Lu, G.-J. Ji, Z.-T. Huang, O. Meth-Cohn, J. Colby, Tetrahedron Asymmetry 2000, 11, 1123;
30. b) M.-X. Wang, J.-J. Li, G.-J. Ji, J.-S. Li, J. Mol. Cat. B: Enzym. 2001, 14, 77;
31. c) M.-X. Wang, S.-J. Lin, Tetrahedron Lett. 2001, 42, 6501;
32. d) , M.-X. Wang, S.-J. Lin, J. Org. Chem. 2002, 67, 6542;
33. e) M.-X. Wang, S.-M. Zhao, Tetrahedron Lett. 2002, 43, 6617;
34. f) M.-X. Wang, S.-M. Zhao, Tetrahedron Asymmetry 2002, 13, 1695.
35. M.-X. Wang, C.-S. Liu, J.-S. Li, Tetrahedron Asymmetry 2001, 12, 3367.
36. M.-X. Wang, G.-Q. Feng, New J. Chem. 2002, 26, 1575.
37. M.-X Wang, G.-Q. Feng, J. Org. Chem. 2003, 68, 621.