Chemoenzymatic dynamic kinetic resolution as a key step in the enantioselective synthesis of (S)-salbutamol

Collection of Czechoslovak Chemical Communications

Volumn 76, Issue 7, 2011, Pages 919-927

  Träff, Annika ^a   Solarte, Carmen E ^b   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b UNIVERSITY OF LLEIDA   (Spain)

Author keywords

Asymmetric synthesis; Dynamic kinetic resolution; Enzymatic catalysis; Kinetic resolution; Racemization

Indexed keywords

EID: 79960199603     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc2011029     Document Type: Article

References (28)

1. McKeage K., Keam S. J.: Drugs 2009, 69, 1799.
2. Gupta M. K., Singh M.: Indian J. Pediatr. 2007, 74, 161.
3. Libretto S. E.: Toxicology 1994, 8, 213.
4. Breuer M., Ditrich K., Habicher T., Hauer B., Kesseler M., Stuermer R., Zelinski T.: Angew. Chem. Int. Ed. 2004, 43, 788.
5. Kamal A., Azhar M. A., Krishnaji T., Malik M. S., Azeeza S.: Coord. Chem. Rev. 2008, 252, 569.
6. Stecher H., Faber K.: Synthesis 1997, 1.
7. For reviews on DKR see: Huerta F. F, Minidis A. B. E., Bäckvall J.-E.: Chem. Soc. Rev. 2001, 30, 321;
8. Kim M.-J., Ahn Y., Park J.: Curr. Opin. Biotechnol. 2002, 13, 578;
9. Pamies O., Bäckvall J.-E.: Chem. Rev. 2003, 103, 3247;
10. Martín-Matute B., Bäckvall J.-E.: Curr. Opin. Chem. Biol. 2007, 11, 226;
11. Ahn Y., Ko S.-B., Kim M.-J., Park J.: Coord. Chem. Rev. 2008, 252, 647;
12. f) Lee J. H., Han K., Kim M.-J., Park J.: Eur. J. Org. Chem. 2010, 999.
13. a) Martín-Matute B., Edit M., Bogár K., Bäckvall J.-E.: Angew. Chem. Int. Ed. 2004, 43, 6535;
14. Martín-Matute B., Edit M., Bogár K., Kaynak F. B., Bäckvall J.-E.: J. Am. Chem. Soc. 2005, 127, 8817.
15. a) Hett R., Fang Q. K., Gao Y., Hong Y., Butler H. T., Nie X., Wald S. A.: Tetrahedron Lett. 1997, 38, 1125;
16. Hett R., Senanayake C. H., Wald S. A.: Tetrahderon Lett. 1998, 39, 1705;
17. Hett R., Stare R., Helqvist P.: Tetrahedron Lett. 1994, 35, 9375;
18. Hong Y., Gao Y., Nie X., Zepp C. M.: Tetrahedron Lett. 1994, 35, 5551.
19. a) Procopiou P. A., Morton G. E., Todd M., Webb G.: Tetrahedron: Asymmetry 2001, 12, 2005;
20. Goswami J., Bezbaruah R. L., Goswami A., Borthakur N.: Tetrahedron: Asymmetry 2001, 12, 3343.
21. Liu J., Zhou D., Jia X., Huang L., Li X., Chan A. S.: Tetrahedron: Asymmetry 2008, 19, 1824.
22. a) Hartley D., Middlemiss D.: J. Med. Chem. 1971, 14, 895;
23. Caira M. R., Hunter R., Nassimbeni L. R., Stevens A. T.: Tetrahedron: Asymmetry 1999, 10, 2175.
24. Babad E., Carruthers N. I., Jaret R. S., Steinman M.: Synthesis 1988, 966.
25. Gribble G. W.: Chem. Soc. Rev. 1998, 27, 395.
26. a) Träff A., Bogár K., Warner M., Bäckvall J.-E.: Org. Lett. 2008, 10, 4807;
27. Johnston E., Bogár K., Bäckvall J.-E.: J. Org. Chem. 2010, 75, 4596.
28. D 20 -37.9 (c 1, MeOH) for (R)-salbutamol 97% ee.