Synthesis of a neonicotinoide pesticide derivative via chemoenzymatic dynamic kinetic resolution

Journal of Organic Chemistry

Volumn 74, Issue 19, 2009, Pages 7407-7410

  Krumlinde, Patrik ^a   Bogár, Krisztián ^b   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

CATALYST LOADINGS; CHEMICAL EQUATIONS; DYNAMIC KINETIC RESOLUTION; ENANTIOMERIC EXCESS; ENZYME CATALYSIS; NEONICOTINOIDS; PESTICIDE DERIVATIVES;

PESTICIDES;

IMIDACLOPRID; RUTHENIUM;

ARTICLE; CHEMOENZYMATIC DYNAMIC KINETIC RESOLUTION; CONTROLLED STUDY; ENANTIOMER; HYDROLYSIS; KINETICS; SYNTHESIS;

EID: 70349456660     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9014276     Document Type: Article

References (25)

1. (a) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.;Wiley-VCH: New York, 2000.
2. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
3. Pàmies, O.; Bäckvall, J. -E. Chem. Rev. 2003, 3247-3262.
4. (a) Martín-Matute, B.; Edin, M.; Bogár, K.; Kaynak, F. B.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 8817-8825.
5. (b) Choi, J. H.; Choi, Y. K.; Kim, Y. H.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972-1977.
6. (c) Martín-Matute, B.; Bäckvall, J.-E. Curr. Opin. Chem. Biol. 2007, 11, 226-232.
7. (a) Paetzold, J.; Bäckvall, J. -E. J. Am. Chem. Soc. 2005, 127, 17620-17621.
8. (b) Thalén, L. K.; Zhao, D.; Sortais, J. B.; Paetzold, J.; Hoben, C.; Bäckvall, J. -E. Chem.-Eur. J. 2009, 15, 3403-3410.
9. (c) Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668-669.
10. (d) Choi, Y. K.; Kim, M. J.; Ahn, Y.; Kim, M. J. Org. Lett. 2001, 3, 4099-4101.
11. Strübing, D.; Krumlinde, P.; Bäckvall, J. -E. Adv. Synth. Catal. 2007, 349, 1577-1581.
12. Jeschkel, P.; Nauen, R. Pest Manage. Sci. 2008, 64, 1084-1098.
13. Matsuda, K.; Buckingham, S. D.; Kleier, D.; Rauh, J. J.; Grauso, M.; Sattelle, D. B. Trends Pharmacol. Sci. 2001, 22, 573-580.
14. Kagabu, S.; Kiriyama, K.; Nishiwaki, H.; Kumamoto, Y.; Tada, T.; Nishimura, K. Biosci. Biotechnol. Biochem. 2003, 67, 980-988.
15. Kuo, D. L. Tetrahedron 1992, 48, 9233-9236.
16. For a scale-up synthesis of 5 to 100 g with this method, see: Lee, C. -H.; Jiang, M.; Cowart, M.; Gfesser, G.; Perner, R.; Kim, K. H.; Gu, Y. G.; Williams, M.; Jarvis, M. F.; Kowaluk, E. A.; Stewart, A. O.; Bhagwat, S. S. J. Med. Chem. 2001, 44, 2133-2138.
17. For transesterification in organic solvents, see: (a) Faber, K. Biotransformations in Organic Chemistry, 5th ed.; Springer: Berlin, 2004.
18. (b) Bornscheuer, U. T., Kazlauskas, R. J. Hydrolases in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2005.
19. It is important to point out that this method requires full conversion in the DKR reaction (>99%); otherwise the nonconverted racemic alcohol will deteriorate the ee after hydrolysis.
20. Uenishi, J.; Hamada, M.; Aburatani, S.; Matsui, K.; Yonemitsu, O.; Tsukube, H. J. Org. Chem. 2004, 69, 6781-6789.
21. At -18 °C no loss of ee or decomposition could be detected after 1 month.
22. (a) Allen, A. D.; Kanagasabapathy, V. M.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 4513-4519.
23. (b) Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1383-1396.
24. (c) Zieger, H. E.; Bright, D. A.; Haubenstock, H. J. Org. Chem. 1986, 51, 1180-1184.
25. (d) Lim, C.; Kim, S. -H.; Yoh, S. -D.; Fujio, M.; Tsuno, Y. Tetrahedron Lett. 1997, 38, 3243-3246.