Dynamic kinetic resolution of racemic β-haloalcohols: Direct access to enantioenriched epoxides

Journal of the American Chemical Society

Volumn 130, Issue 41, 2008, Pages 13508-13509

  Haak, Robert M ^a   Berthiol, Florian ^a   Jerphagnon, Thomas ^a   Gayet, Arnaud J A ^a   Tarabiono, Chiara ^b   Postema, Christiaan P ^b   Ritleng, Vincent ^a   Pfeffer, Michel ^c   Janssen, Dick B ^b   Minnaard, Adriaan J ^a   Feringa, Ben L ^a   De Vries, Johannes G ^a,d  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BETA HALOALCOHOL DERIVATIVE; CYSTEINE; ENZYME; EPOXIDE; HALOALCOHOL; PROTEIN HHEC; SERINE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DYNAMIC KINETIC RESOLUTION; ENANTIOMER; ENZYME STABILITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; RACEMIC MIXTURE; RACEMIZATION; STEREOCHEMISTRY;

ALCOHOLS; CATALYSIS; CYCLIZATION; EPOXY COMPOUNDS; HALOGENS; KINETICS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 53849084492     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805128x     Document Type: Article

References (28)

1. For recent reviews on DKR, see:(a) Ahn, Y.; Ko, S.-B.; Kim, M.-J.; Park, J. Coord. Chem. Rev. 2008, 252, 647-658.
2. (b) Pellissier, H. Tetrahedron 2008, 64, 1563-1601.
3. (c) Martín-Matute, B.; Bäckvall, J.-E. Curr. Opin. Chem. Biol. 2007, 11, 226-232.
4. (d) Kim, M.-J.; Ahn, Y.; Park, J. Bull. Korean Chem. Soc. 2005, 26, 515-522.
5. (e) Pàmies, O.; Bäckvall, J.-E. Trends Biotechnol. 2004, 22, 130-135.
6. (f) Turner, N. J. Curr. Opin. Chem. Biol. 2004, 8, 114-119.
7. (g) Pàmies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247-3261.
8. (a) Larsson, A. L. E.; Persson, B. A.; Bäckvall, J.-E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1211-1212.
9. (b) Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 37, 7623-7626.
10. Pàmies, O.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 9006-9010.
11. Haak, R. M.; Tarabiono, C.; Janssen, D. B.; Minnaard, A. J.; De Vries, J. G.; Feringa, B. L. Org. Biomol. Chem. 2007, 5, 318-323.
12. For reviews on haloalcohol dehalogenases, see:(a) Janssen, D. B. Adv. Appl. Microbiol. 2007, 61, 233-252.
13. (b) De Jong, R. M.; Dijkstra, B. W. Curr. Opin. Struct. Biol. 2003, 13, 722-730.
14. (c) De Vries, E. J.; Janssen, D. B. Curr. Opin. Biotechnol. 2003, 14, 414-420.
15. (d) Fetzner, S.; Lingens, F. Microbiol. Rev. 1994, 58, 641-685.
16. Hasnaoui-Dijoux, G.; Majeríc Elenkov, M.; Lutje Spelberg, J. H.; Hauer, B.; Janssen, D. B. ChemBioChem 2008, 9, 1048-1051.
17. This evaluation is part of a forthcoming paper on racemization reactions catalyzed by a range of iridacycles. See the Supporting Information for racemization results using a number of ruthenium-based catalysts.
18. Sortais, J.-B.; Pannetier, N.; Holuigue, A.; Barloy, L.; Sirlin, C.; Pfeffer, M.; Kyritsakas, N. Organometallics 2007, 26, 1856-1867.
19. Liu, J.; Wu, X.; Iggo, J. A.; Xiao, J. Coord. Chem. Rev. 2008, 252, 782-809.
20. Martín-Matute, B.; Edin, M.; Bogár, K.; Kaynak, F. B.; Bäckvall, J.-E. J. Am. Chem. Soc. 2005, 127, 8817-8825.
21. Haloketone formation was not observed in subsequent DKR experiments using a variety of haloalcohols.
22. Tang, L.; Van Hylckama Vlieg, J. E. T.; Lutje Spelberg, J. H.; Fraaije, M. W.; Janssen, D. B. Enzyme Microb. Technol. 2002, 30, 251-258.
23. (a) Majeríc Elenkov, M.; Tang, L.; Hauer, B.; Janssen, D. B. Org. Lett. 2006, 8, 4227-4229.
24. (b) Tang, L.; Torres Pazmiño, D. E.; Fraaije, M. W.; De Jong, R. M.; Dijkstra, B. W.; Janssen, D. B. Biochemistry 2005, 44, 6609-6618.
25. (c) Tang, L.; Van Merode, A. E. J.; Lutje Spelberg, J. H.; Fraaije, M. W.; Janssen, D. B. Biochemistry 2003, 42, 14057-14065.
26. Addition of the catalyst solution in one portion at the beginning of the reaction led to poorer yields and enantioselectivities.
27. Carter, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153-203.
28. In most cases conversion stopped at around 75-90%, which can be attributed to the fact that the ring-closure reaction is reversible. See also: Lutje Spelberg, J. H.; Van Hylckama Vlieg, J. E. T.; Bosma, T.; Kellogg, R. M.; Janssen, D. B Tetrahedron: Asymmetry 1999, 10, 2863-2870.