Chemo-enzymatic synthesis of key intermediates (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactone via lipase-mediated Baeyer-Villiger oxidation of levoglucosenone

Green Chemistry

Volumn 17, Issue 1, 2015, Pages 404-412

  Flourat, A L ^a,b   Peru, A A M ^a,b   Teixeira, A R S ^a,c   Brunissen, F ^a,b   Allais, F ^a,c  

^a AGROPARISTECH   (France)

^b INSTITUT JEAN PIERRE BOURGIN   (France)

^c Université Paris Saclay   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85030247283     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c4gc01231c     Document Type: Article

References (45)

1. A. Corma, S. Iborra and A. Velty, Chem. Rev., 2007, 107, 2411.
2. G. W. Huber, S. Iborra and A. Corma, Chem. Rev., 2006, 106, 4044.
3. (a) M. S. Miftakhov, F. A. Valeev and I. N. Gaisina, Russ. Chem. Rev., 1994, 63, 869;
4. (b) A. V. Bridgwater, D. Meier and D. Radlein, Org. Geochem., 1999, 30, 1479;
5. (c) Q. Lu, W. M. Xiong, W. Z. Li, Q. X. Guo and X. F. Zhu, Bioresour. Technol., 2009, 100, 4871.
6. (a) F. Shafizadeh, R. H. Furneaux, T. T. Stevenson and T. G. Cochran, Carbohydr. Res., 1978, 61, 519;
7. (b) G. Dobele, T. Dizhbite, G. Rossinskaja, G. Telysheva, D. Mier, S. Radtke and O. Faix, J. Anal. Appl. Pyrolysis, 2003, 68-69, 197;
8. (c) J. Zandersons, A. Zhurinsh, G. Dobele, V. Jurkjane, J. Rizhikovs, B. Spince and A. Pazhe, J. Anal. Appl. Pyrolysis, 2013, 103, 222.
9. J. Jae, G. A. Tompsett, A. J. Foster, K. D. Hammond, S. M. Auerbach, R. F. Lobo and G. W. Huber, J. Catal., 2011, 279, 257.
10. G. R. Court, C. H. Lawrence, W. D. Raverty and A. J. Duncan, WO2011/000030, 2011.
11. (a) V. L. Budarin, P. S. Shuttleworth, J. R. Dodson, A. J. Hunt, B. Lanigan, R. Marriott, K. J. Milkowski, A. J. Wilson, S. W. Breeden, J. Fan, E. H. K. Sin and J. H. Clark, Energy Environ. Sci., 2011, 4, 471;
12. (b) X. Hu, L. Wu, Y. Wang, D. Mourant, C. Lievens, R. Gunawan and C. Z. Li, Green Chem., 2012, 14, 3087.
13. (a) K. Tomioka, T. Ishiguro and K. Koga, J. Chem. Soc., Chem. Commun., 1979, 652;
14. (b) D. Enders, V. Lausberg, G. Del Signore and O. M. Berner, Synthesis, 2002, 515.
15. E. Takashi, M. Katsuya, Y. Hajime, K. Koseki, H. Kawakami and H. Matsushita, Heterocycles, 1990, 31, 1585.
16. (a) H. Hawakami, T. Ebata, K. Koseki, K. Statsumoto, H. Matsushita, Y. Naoi and K. Itoh, Heterocycles, 1990, 31, 2041;
17. (b) R. Flores, A. Rustullet, R. Alibes, A. Alvarez-Larena, P. de March, M. Figueredo and J. Font, J. Org. Chem., 2011, 76, 5369;
18. (c) A. Diaz-Rodriguez, Y. S. Sanghvi, S. Fernandez, R. F. Schinazi, E. A. Theodorakis, M. Ferreroa and V. Gotor, Org. Biomol. Chem., 2009, 7, 1415.
19. K. Koseki, T. Ebata, H. Kawakawmi, H. Matsushita, K. Itoh and Y. Naoi, US 4,9947,585, Feb. 19th, 1991.
20. (a) C. Paris, M. Moliner and A. Corma, Green Chem., 2013, 15, 2101;
21. (b) P. Rammohan, S. Taradas and K. Shampa, ARKIVOC, 2012, 570;
22. (c) K. Tanabe and W. F. Hölderich, Appl. Catal. A., 1999, 181, 399;
23. (d) J. H. Clark, Acc. Chem. Res., 2002, 35, 791;
24. (e) Y. C. Sharma, B. Singh and J. Korstad, Biofuels, Bioprod. Bioref., 2011, 5, 69.
25. (a) P. Carlqvist, R. Eklund, K. Hult and T. Brinck, J. Mol. Model., 2003, 9(3), 164;
26. (b) M. Y. Rios, E. Salazar and H. F. Olivo, Green Chem., 2007, 9, 459;
27. (c) M. Y. Rios, E. Salazar and H. F. Olivo, J. Mol. Catal. B: Enzym., 2008, 54, 61;
28. (d) A. J. Kotlewska, F. van Rant-wijk, R. A. Sheldon and I. W. C. E. Arends, Green Chem., 2011, 13, 2154;
29. (e) A. Drozdz, A. Chrobok, S. Baj, K. Szymanska, J. Mrowiec-Bialon and A. B. Jarzebski, Appl. Catal., A, 2013, 467, 163;
30. (f) G. Chavez, R. Hatti-Kaul, R. A. Sheldon and G. Mamo, J. Mol. Catal. B: Enzym., 2013, 89, 67.
31. (a) F. Pion, F. A. Reano, P.-H. Ducrot and F. Allais, RSC Adv., 2013, 3, 8988;
32. (b) F. Pion, P.-H. Ducrot and F. Allais, Macromol. Chem. Phys., 2014, 5, 431.
33. K. Alfonsi, J. Colberg, P. J. Dunn, T. Fevig, S. Jennings, T. Johnson, P. Kleine, C. Knight, M. A. Nagy, D. Perry and M. Stefaniakc, Green Chem., 2007, 10, 31-36.
34. K. Koseki, T. Ebata, H. Kawakawmi, H. Matsushita, K. Itoh and Y. Naoi, US 5,112,994, 1992.
35. (a) C. Orellana, S. Camocho, D. Adlercreutz, B. Mattiason and R. Hatti-Kaul, Eur. J. Lipid Sci. Technol., 2005, 107, 864;
36. (b) S. Bhattachayra, A. Drews, E. Lyagin, M. Kraume and M. B. Ansorge-Schumacher, Chem. Eng. Technol., 2012, 35, 1.
37. (a) U. Törnvall, C. Melin, R. Hatti-Kaul and M. Hedström, Rapid Commun. Mass Spectrom., 2009, 2959;
38. (b) U. Törnvall, M. Hedström, K. Schilléen and R. Hatti-Kaul, Biochimie, 2010, 92, 1867.
39. A. R. Katrizky, N. G. Akhmedov and O. V. Denisko, Magn. Reson. Chem., 2003, 41, 37.
40. (a) J. Sun, Y. Jiang, L. Zhou and J. Gao, New Biotechnol., 2010, 24, 53;
41. (b) M. Adamczak, Pol. J. Food Nutr. Sci., 2003, 4, 3.
42. (a) K. Rezaei, Crit. Rev. Biotechnol., 2007, 27(4), 183;
43. (b) P. Adlercreutz, in Organic Synthesis with Enzymes in Non-Aqueous Media, ed. G. Carrea and S. Riva, Wiley-VCH Verlag Gmbh & Co KGaA, Weinheim, Germany, 2008, pp. 3-24;
44. (c) A. M. Klibanov, Nature, 2001, 409, 241.
45. (a) I. Bonnaventure and A. B. Charette, J. Org. Chem., 2008, 16, 6330;