A new environmentally friendly method for the Baeyer-Villiger oxidation of cyclobutanones catalyzed by thioureas using H2O2 as an oxidant

RSC Advances

Volumn 2, Issue 15, 2012, Pages 6135-6139

  Sasakura, Niiha ^a   Nakano, Keiji ^a   Ichikawa, Yoshiyasu ^a   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDANTS; THIOUREAS;

BAEYER VILLIGER OXIDATION; CYCLOBUTANONES; GAMMA BUTYROLACTONE; HIGH YIELD;

KETONES;

EID: 84863963912     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c2ra20898a     Document Type: Article

References (51)

1. A. Baeyer V. Villiger Ber. 1899 32 3625
2. L. Kürti and B. Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, pp 28-29
3. G. R. Krow Org. React. 1993 43 251
4. G. Strukul Angew. Chem., Int. Ed. 1998 37 1198
5. M. Renz B. Meunier Eur. J. Org. Chem. 1999 737
6. Catalytic Oxidations with Hydrogen Peroxide as Oxidant, ed., G. Strukul, Kluwer Academic, Dordrecht, 1992
7. R. Noyori M. Aoki K. Sato Chem. Commun. 2003 1977
8. J. Piera J.-E. Bäckvall Angew. Chem., Int. Ed. 2008 47 3506
9. R. A. Michelin P. Sgarbossa A. Scarso G. Strukul Coord. Chem. Rev. 2010 254 646
10. H. Pellissier Tetrahedron 2007 63 9267
11. C. F. Barbas III Angew. Chem., Int. Ed. 2008 47 42
12. H. Kotsuki H. Ikishima A. Okuyama Heterocycles 2008 75 493
13. H. Kotsuki H. Ikishima A. Okuyama Heterocycles 2008 75 757
14. A. Dondoni A. Massi Angew. Chem., Int. Ed. 2008 47 4638
15. P. Melchiorre M. Marigo A. Carlone G. Bartoli Angew. Chem., Int. Ed. 2008 47 6138
16. S. Bertelsen K. A. Jorgensen Chem. Soc. Rev. 2009 38 2178
17. G. Valero X. Companyó N. Bravo A.-N. Alba A. Moyano R. Rios Synlett 2010 1883
18. A. Moyano R. Rios Chem. Rev. 2011 111 4703
19. G.-J. ten Brink I. W. C. E. Arends R. A. Sheldon Chem. Rev. 2004 104 4105
20. T. Seiser T. Saget D. N. Tran N. Cramer Angew. Chem., Int. Ed. 2011 50 7740
21. Y. Imada H. Iida S.-I. Murahashi T. Naota Angew. Chem., Int. Ed. 2005 44 1704
22. S. Xu Z. Wang X. Zhang X. Zhang K. Ding Angew. Chem., Int. Ed. 2008 47 2840
23. S. Xu Z. Wang Y. Li X. Zhang H. Wang K. Ding Chem.-Eur. J. 2010 16 3021
24. S. Xu Z. Wang X. Zhang K. Ding Eur. J. Org. Chem. 2011 110
25. P. R. Schreiner Chem. Soc. Rev. 2003 32 289
26. Y. Takemoto Org. Biomol. Chem. 2005 3 4299
27. T. Akiyama J. Itoh K. Fuchibe Adv. Synth. Catal. 2006 348 999
28. M. S. Taylor E. N. Jacobsen Angew. Chem., Int. Ed. 2006 45 1520
29. S. J. Connon Chem.-Eur. J. 2006 12 5418
30. A. G. Doyle E. N. Jacobsen Chem. Rev. 2007 107 5713
31. H. Miyabe Y. Takemoto Bull. Chem. Soc. Jpn. 2008 81 785
32. S. J. Connon Chem. Commun. 2008 2499
33. S. J. Connon Synlett 2009 354
34. K. Etzenbach-Effers A. Berkessel Top. Curr. Chem. 2010 291 1
35. K. Mori J. Maddaluno K. Nakano Y. Ichikawa H. Kotsuki Synlett 2009 2346
36. K. Mori T. Yamauchi J. Maddaluno K. Nakano Y. Ichikawa H. Kotsuki Synlett 2011 2080
37. M. Kotke P. R. Schreiner Tetrahedron 2006 62 434
38. H. Y. Kim K. Oh Org. Lett. 2011 13 1306.
39. F. Z. Dorwald, J. B. Hansen, J. P. Mogensen, T. M. Tagmose, B. Pirotte, P. Lebrun, P. De Tullio, S. Boverie and J. Delarge, US Pat, 1997, 55193
40. A. A. Rodriguez H. Yoo J. W. Ziller K. J. Shea Tetrahedron Lett. 2009 50 6830
41. I. Saito R. Nagata K. Yuba T. Matsuura Tetrahedron Lett. 1983 24 1737
42. J. Lao X. Zhang J. Wang X. Li M. Yan H. Luo Tetrahedron: Asymmetry 2009 20 2818
43. R. Criegee, Houben-Weyl, Vol. VIII, Georg Thieme Verlag, Stuttgart, 1968, pp 1-74
44. A. Lattanzi Synlett 2007 2106.
45. M. Shi X.-G. Liu Org. Lett. 2008 10 1043
46. T. Shinohara S. Fujioka H. Kotsuki Heterocycles 2001 55 237
47. H.-J. Xu F.-F. Zhu Y.-Y. Shen X. Wan Y.-S. Feng Tetrahedron 2012 68 4145
48. T. Satoh Y. Kamide S. Sugiyama Tetrahedron 2004 60 11805
49. L. J. Gooen D. M. Ohlmann M. Dierker Green Chem. 2010 12 197
50. S. Fuchs V. Berl J.-P. Lepoittevin Eur. J. Org. Chem. 2007 1145
51. M. Aoki D. Seebach Helv. Chim. Acta 2001 84 187