Facile preparation of oxazole-4-carboxylates and 4-ketones from aldehydes using 3-oxazoline-4-carboxylates as intermediates

Organic Letters

Volumn 12, Issue 15, 2010, Pages 3456-3459

  Murai, Kenichi ^a   Takahara, Yusuke ^a   Matsushita, Tomoyo ^a   Komatsu, Hideyuki ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALDEHYDES; CARBOXYLIC ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; KETONES; MOLECULAR STRUCTURE; OXAZOLES;

EID: 77955141992     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1012789     Document Type: Article

References (62)

1. Jansen, R.; Irschik, H.; Reichenbach, H.; Wray, V.; Hoefle, G. Liebigs Ann. Chem. 1994, 759
2. Hopkins, C. D.; Wipf, P. Nat. Prod. Rep. 2009, 26, 585
3. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc. 1991, 113, 3173
4. For recent reviews, see: Yeh, V. S. C. Tetrahedron 2004, 60, 11995
5. Jin, Z. Nat. Prod. Rep. 2006, 23, 464
6. Jin, Z. Nat. Prod. Rep. 2009, 26, 382
7. For examples, see: Wipf, P.; Graham, T. H. J. Am. Chem. Soc. 2004, 126, 15346
8. Hartung, I. V.; Niess, B.; Haustedt, L. O.; Hoffmann, H. M. R. Org. Lett. 2002, 4, 3239
9. Hillier, M. C.; Park, D. H.; Price, A. T.; Ng, R.; Meyers, A. I. Tetrahedron Lett. 2000, 41, 2821
10. Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 4924
11. Yokokawa, F.; Asano, T.; Shioiri, T. Tetrahedron 2001, 57, 6311
12. Smith, T. E.; Kuo, W.-H.; Balskus, E. P.; Bock, V. D.; Roizen, J. L.; Theberge, A. B.; Carroll, K. A.; Kurihara, T.; Wessler, J. D. J. Org. Chem. 2007, 73, 142
13. Lachia, M.; Moody, C. J. Nat. Prod. Rep. 2008, 25, 227
14. Custar, D. W.; Zabawa, T. P.; Hines, J.; Crews, C. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 12406
15. Deeley, J.; Bertram, A.; Pattenden, G. Org. Biomol. Chem. 2008, 6, 1994
16. Zhang, J.; Polishchuk, E. A.; Chen, J.; Ciufolini, M. A. J. Org. Chem. 2009, 74, 9140
17. Cheung, C.-M.; Goldberg, F. W.; Magnus, P.; Russell, C. J.; Turnbull, R.; Lynch, V. J. Am. Chem. Soc. 2007, 129, 12320
18. Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165
19. Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267
20. Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 907
21. Yokokawa, F.; Shioiri, T. Tetrahedron Lett. 2002, 43, 8679
22. Sakakura, A.; Kondo, R.; Ishihara, K. Org. Lett. 2005, 7, 1971
23. Williams, D. R.; Lowder, P. D.; Gu, Y.-G.; Brooks, D. A. Tetrahedron Lett. 1997, 38, 331
24. Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.; Anzai, M.; Ando, A.; Shioiri, T. Synlett 1998, 35
25. Meyers, A. I.; Tavares, F. Tetrahedron Lett. 1994, 35, 2481
26. Meyers, A. I.; Tavares, F. X. J. Org. Chem. 1996, 61, 8207
27. Tavares, F.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 6803
28. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604
29. Brain, C. T.; Paul, J. M. Synlett 1999, 1642
30. Pulici, M.; Quartieri, F.; Felder, E. R. J. Comb. Chem. 2005, 7, 463
31. For recent progress on synthesis of various substituted oxazole derivatives, see: Williams, D. R.; Fu, L. Org. Lett. 2010, 12, 808
32. Ackermann, L.; Barfus̈ser, S.; Pospech, J. Org. Lett. 2010, 12, 724
33. Lee, K.; Counceller, C. M.; Stambuli, J. P. Org. Lett. 2009, 11, 1457
34. Santos, A.; dos; Kaïm, L. E.; Grimaud, L.; Ronsseray, C. Chem. Commun. 2009, 3907
35. Verrer, C.; Hoarau, C.; Marsais, F. Org. Biomol. Chem. 2009, 7, 647
36. Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2008, 10, 2717
37. Besseliev̀re, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029
38. Chudasama, V.; Wilden, J. D. Chem. Commun. 2008, 3768
39. Riedrich, M.; Harkal, S.; Arndt, H.-D. Angew. Chem., Int. Ed. 2007, 46, 2701
40. Martín, R.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 5521
41. Ferrer Flegeau, E.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2006, 8, 2495
42. Keni, M.; Tepe, J. J. J. Org. Chem. 2005, 70, 4211
43. Coqueron, P.-Y.; Didier, C.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2003, 42, 1411
44. Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905
45. For limited examples of the oxidation of 2-aryl-oxazolidines derived from aldehydes to give oxazoles, see: Badr, M. Z. A.; Aly, M. M.; Fahmy, A. M.; Mansour, M. E. Y. Bull. Chem. Soc. Jpn. 1981, 54, 1844
46. Fujioka, H.; Murai, K.; Ohba, Y.; Hiramatsu, A.; Kita, Y. Tetrahedron Lett. 2005, 46, 2197
47. Fujioka, H.; Murai, K.; Kubo, O.; Ohba, Y.; Kita, Y. Tetrahedron 2007, 63, 638
48. Murai, K.; Morishita, M.; Nakatani, R.; Kubo, O.; Fujioka, H.; Kita, Y. J. Org. Chem. 2007, 72, 8947
49. Murai, K.; Morishita, M.; Nakatani, R.; Fujioka, H.; Kita, Y. Chem. Commun. 2008, 4498
50. Murai, K.; Takaichi, N.; Takahara, Y.; Fukushima, S.; Fujioka, H. Synthesis 2010, 520
51. Schwekendiek, K.; Glorius, F. Synthesis 2006, 2996
52. Ishihara, M.; Togo, H. Tetrahedron 2007, 63, 1474
53. Sayama, S. Synlett 2006, 1479
54. Favreau, S.; Lizzani-Cuvelier, L.; Loiseau, M.; Duñch, E.; Fellous, R. Tetrahedron Lett. 2000, 41, 9787
55. Dömling, A.; Bayler, A.; Ugi, I. Tetrahedron 1995, 51, 755
56. Hua, D. H.; Khiar, N.; Zhang, F.; Lambs, L. Tetrahedron Lett. 1992, 33, 7751
57. 3 was used as an acid scavenger for HBr formed in situ.
58. For examples of the reaction of 1,3-oxazolidines with Grignard reagents, see: Steinig, A. G.; Spero, D. M. J. Org. Chem. 1999, 64, 2406
59. Yamauchi, T.; Takahashi, H.; Higashiyama, K. Heterocycles 1998, 48, 1813
60. Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340
61. Takahashi, H.; Chida, Y.; Yoshii, T.; Suzuki, T.; Yanaura, S. Chem. Pharm. Bull. 1986, 34, 2071
62. Several attempts at the one-pot transformation of aldehydes to oxazoles have failed at this stage.