Chemo-enzymatic Baeyer-Villiger oxidation of cyclopentanone and substituted cyclopentanones

Journal of Molecular Catalysis B: Enzymatic

Volumn 54, Issue 3-4, 2008, Pages 61-66

  Rios, María Yolanda ^a   Salazar, Enrique ^a   Olivo, Horacio F ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

Baeyer Villiger oxidation; Candida antarctica lipase B; Chemo enzymatic oxidation; Trans esterification

Indexed keywords

CATALYTIC OXIDATION; CHEMICAL OXYGEN DEMAND; ESTERS; HYDROGEN; HYDROGEN PEROXIDE; UREA;

BAEYER VILLIGER OXIDATIONS; CANDIDA ANTARCTICA; CATALYTIC AMOUNTS; CYCLOHEXANONES; CYCLOPENTANONE; ELSEVIER (CO); ENZYMATIC OXIDATIONS; ETHYL ACETATE (ETAC); UREA HYDROGEN PEROXIDE;

OXIDATION;

CYCLOPENTANONE DERIVATIVE; HYDROGEN PEROXIDE; LACTONE DERIVATIVE; LIPASE B; UREA;

ARTICLE; BAEYER VILLIGER REACTION; CANDIDA ANTARCTICA; NUCLEAR MAGNETIC RESONANCE; OXIDATION; TRANSESTERIFICATION;

CANDIDA ANTARCTICA;

EID: 47549095262     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2007.12.012     Document Type: Article

References (46)

1. Moonen M.J.H., Westphal A.H., Rietjens I.M.C.M., and van Berkel W.J.H. Adv. Synth. Catal. 347 (2005) 1027-1034
2. Ten Brink G.-J., Arends I.W.C.E., and Sheldon R.A. Chem. Rev. 104 (2004) 4105-4123
3. Renz M., and Meunier B. Eur. J. Org. Chem. 4 (1999) 737-750
4. Lemoult S.C., Richardson P.F., and Roberts S.M. J. Chem. Soc. Perkin, Trans. 1 (1995) 89-91
5. Krow G.R. Org. React. 42 (1993) 251-798
6. Krow G.R. Org. React. 37 (1981) 2697-2702
7. Watanabe A., Uchida T., Ito K., and Katsuki T. Tetrahedron Lett. 43 (2002) 4481-4485
8. Strukul G. Angew. Chem. Int. Ed. 37 (1998) 1198-1209
9. Bolm C., Schlingloff G., and Weickhardt K. Angew. Chem. Int. Ed. 33 (1994) 1848-1849
10. Gusso A., Baccin C., Pinna F., and Strukul G. Organometallics 13 (1994) 3442-3451
11. de Gonzalo G., Ottolina G., Zambianchi F., Fraaije M.W., and Carrea G. J. Mol. Catal. B: Enzym. 39 (2006) 91-97
12. Mihovilovic M.D., Snajdrova R., and Groötzl B. J. Mol. Catal. B: Enzym. 39 (2006) 135-140
13. Mihovilovic M.D. Curr. Org. Chem. 10 (2006) 1265-1287
14. Ottolina G., de Gonzalo G., Carrea G., and Daniela B. Adv. Synth. Catal. 347 (2005) 1035-1040
15. Mihovilovic M.D., Rudroff F., and Grötzl B. Curr. Org. Chem. 8 (2004) 1057-1069
16. Kamerbeek N.M., Janssen D.B., van Berkel W.J.H., and Fraaije M.W. Adv. Synth. Catal. 345 (2003) 667-678
17. Mihovilovic M.D., Müller B., Kayser M.M., Stewart J.D., and Stanetty P. Synlett (2002) 700-702
18. Stewart J.D. Curr. Org. Chem. 2 (1998) 211-232
19. Roberts S.M., and Wan P.W.H. J. Mol. Catal. B: Enzym. 4 (1998) 111-136
20. Constable D.J.C., Dunn P.J., Hayler J.D., Humphrey G.R., Leazer Jr. J.L., Linderman R.J., Lorenz K., Manley Ju., Pearlman B.A., Wells A., Zaks A., and Zhang T.Y. Green Chem. 9 (2007) 411-420
21. Rusch gen Klaas M., and Warwell S. In: Bornscheuer U.T. (Ed). Enzymes in Lipid Modification (2000), Wiley-VCH 116-127
22. Ankudey E.G., Olivo H.F., and Peeples T.L. Green Chem. 8 (2006) 923-926
23. Rios M.Y., Salazar E., and Olivo H.F. Green Chem. 9 (2007) 459-462
24. Carboni-Oerlemans C., de Maria P.D., Tuin B., Bargeman G., van der Meer A., and van Genert R. J. Biotechnol. 126 (2006) 140-151
25. Houde A., Kademi A., and Leblanc D. Appl. Biochem. Biotechnol. 118 (2004) 155-170
26. Kirk O., and Christensen M.W. Org. Process Res. Dev. 6 (2002) 446-451
27. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., and Witholt B. Nature 409 (2001) 258-268
28. Anderson E.M., Larsson M.K., and Kirk O. Biocatal. Biotransform. 16 (1998) 181-204
29. Bornscheuer U.T., and Kazlauskas R.J. Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations (2006), Wiley-VCH
30. Rotticci D., Ottosson J., Norin T., and Hult K. Methods Biotechnol. 15 (2001) 261-276
31. Björkling F., Godtfredsen S.E., and Kirk O. Chem. Commun. (1990) 1301-1303
32. Björkling F., Frykman H., Godtfredsen S.E., and Kirk O. Tetrahedron 48 (1992) 4587-4592
33. Moreira M.A., Bitencourt T.B., and Nascimento M.D. Syn. Commun. 35 (2005) 2107-2114
34. Gotor-Fernandez V., and Gotor V. Curr. Org. Chem. 10 (2006) 1125-1143
35. Slotema W.F., Sandoval G., Guieysse D., Straathof A.J.J., and Marty A. Biotechnol. Bioeng. 82 (2003) 664-669
36. Litjens M.J.J., Straathof A.J.J., Jongejan J.A., and Heijnen J.J. Tetrahedron 55 (1999) 12411-12418
37. Hacking M.A.P.J., Wegman M.A., Rops J., van Rantwijk F., and Sheldon R.A. J. Mol. Catal. B: Enzym. 5 (1998) 155-157
38. de Zoete M.C., Kock-van Dalen A.C., Van Rantwijk F., and Sheldon R.A. J. Chem. Soc. Chem. Commun. (1993) 1831-1993
39. Taliansky S. Synlett (2005) 1962-1963
40. Cooper M.S., Heaney H., Newbold A.J., and Sanderson W.R. Synlett (1990) 533-535
41. Skouridou V., Stamatis H., and Kolisis F.N. J. Mol. Catal. B: Enzym. 21 (2003) 67-69
42. Shioji K., Matsuo A., Okuma K., Nakamura K., and Ohno A. Tetrahedron Lett. 41 (2000) 8799-8802
43. Kondaveti L., Al-Azemi T.F., and Bisht K.S. Tetrahedron: Asymmetry 13 (2002) 129-135
44. Lee E., Lee Y.R., Moon B., Kwon O., Shim M.S., and Yun J.S. J. Org. Chem. 59 (1994) 1444-1456
45. We are currently investigating other solvents for this chemo-enzymatic oxidation to explore the possibility of preparing cyclopentanones and valerolactones in enantioenriched form.
46. Wiles C., Watts P., Haswell S.J., and Pombo-Villar E. Tetrahedron 61 (2005) 10757-10773