Iron-catalyzed aminolysis of β-carbonyl 1,3-dithianes: Synthesis of stereodefined β-enaminones and 3,4-disubstituted pyrazoles

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1722-1725

  Wang, Yeming ^a   Bi, Xihe ^a,b   Li, Wei Qi ^c   Li, Dehua ^a   Zhang, Qian ^a   Liu, Qun ^a   Ondon, Brim Stevy ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

^c HARBIN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953202218     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200246x     Document Type: Article

References (46)

1. Sneddon, H. F.; van den Heuvel, A.; Hirsch, A. K. H.; Booth, R. A.; Shaw, D. M.; Gaunt, M. J.; Ley, S. V. J. Org. Chem. 2006, 71, 2715
2. Xu, C.; Bartley, J. K.; Enache, D. I.; Knight, D. W.; Lunn, M.; Lok, M.; Hutchings, G. J. Tetrahedron Lett. 2008, 49, 2454
3. Choi, E. B.; Youn, I. K.; Pak, C. S. Synthesis 1988, 792
4. Mellor, J. M.; Schofield, R.; Korn, S. R. Tetrahedron 1997, 53, 1711
5. Gaunt, M. J.; Sneddon, H. F.; Hewitt, P. R.; Orsini, P.; Hook, D. F.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 15
6. Sneddon, H. F.; Gaunt, M. J.; Ley, S. V. Org. Lett. 2003, 5, 1147
7. Gaunt, M. J.; Hook, D. F.; Tanner, H. R.; Ley, S. V. Org. Lett. 2003, 5, 4815
8. Gaunt, M. J.; Jessiman, A. S.; Orsini, P.; Tanner, H. R.; Hook, D. F.; Ley, S. V. Org. Lett. 2003, 5, 4819
9. For a review, see: Ley, S. V. Tetrahedron 2010, 66, 6270
10. Kang, J.; Liang, F.; Sun, S.-G.; Liu, Q.; Bi, X. Org. Lett. 2006, 8, 2547
11. For reviews on β-enaminones, see: Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433
12. Elassara, A.-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463
13. Greenhill, J. V. Chem. Soc. Rev. 1977, 6, 277
14. Eddingtona, N. D.; Coxa, D. S.; Robertsb, R. R.; Stablesc, J. P.; Powelld, C. B.; Scotte, K. R. Curr. Med. Chem. 2000, 7, 417
15. Recent examples on the synthetic utility of β-enaminones, see: Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078
16. Wan, J.-P.; Pan, Y.-J. Chem. Commun. 2009, 2768
17. Ilangovan, A.; Kumar, R. G. Chem.-Eur. J. 2010, 16, 2938
18. Saito, A.; Konishi, T.; Hanzawa, Y. Org. Lett. 2010, 12, 372
19. Chen, Y.; Ju, T.; Wang, J.; Yu, W.; Du, Y.; Zhao, K. Synlett 2010, 231
20. Lu, J.; Cai, X.; Hecht, S. M. Org. Lett. 2010, 12, 5189
21. For reviews on iron-catalyzed reactions, see: Iron Catalysis in Organic Chemistry: Reactions and Applications; Plietker, B., Ed.; Wiley-VCH: Weinheim, 2008.
22. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2010, 111, 1293
23. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
24. Wang, Y.; Li, W.-Q.; Che, G.; Bi, X.; Liao, P.; Zhang, Q.; Liu, Q. Chem. Commun. 2010, 46, 6843
25. Wang, Y.; Bi, X.; Li, D.; Liao, P.; Wang, Y.; Yang, J.; Zhang, Q.; Liu, Q. Chem. Commun. 2011, 47, 809
26. For example, see: Seko, S.; Tani, N. Tetrahedron Lett. 1998, 39, 8117
27. Luo, B. H.; Guan, H. P.; Hu, C. M. Synlett 1997, 1261
28. Haight, A. R.; Stuk, T. L.; Menzia, J. A.; Robbins, T. A. Tetrahedron Lett. 1997, 38, 4191
29. Lue, P.; Greenhill, J. V. Adv. Heterocycl. Chem. 1997, 67, 215
30. Dominguez, E.; Ibeas, E.; de Maigorta, E. M.; Palacios, J. K.; SanMartin, R. J. Org. Chem. 1996, 61, 5435
31. Hegde, S. G.; Jones, C. R. J. Heterocycl. Chem. 1993, 30, 1501
32. Elnagdi, M. H.; Fahmy, S. M.; Hafez, E. A.; Elmoghayer, M. R. H.; Amer, S. A. R. J. Heterocycl. Chem. 1979, 16, 1109
33. Hogenkamp, D. J.; Johnstone, T. B. C.; Gee, K. W. U.S. Pat. Appl. Publ. 2008/0064748 A1, 2008.
34. Hogenkamp, D. J.; Johnstone, T. B. C.; Gee, K. W. U.S. Pat. Appl. Publ. 2006/0293329 A1, 2006.
35. Seltzman, H. H. Drug Dev. Res. 2009, 70, 601
36. Lin, R.; Chiu, G.; Yu, Y.; Connolly, P. J.; Li, S.; Lu, Y.; Adams, M.; Fuentes-Pesquera, A. R.; Emanuel, S. L.; Greenberger, L. M. Bioorg. Med. Chem. Lett. 2007, 17, 4557
37. Franchini, M. C.; Bonini, B. F.; Camaggi, C. M.; Gentili, D.; Pession, A.; Rani, M.; Strocchi, E. Eur. J. Med. Chem. 2010, 45, 2024
38. Dzhuraev, A. D.; Makhsumov, A. G.; Zakirov, U. B.; Nikbaev, A. T. Pharm. Chem. J. 1987, 21, 718
39. Berdini, V.; O'Brien, M. A.; Carr, M. G.; Early, T. R.; Gill, A. L.; Trewartha, G.; Woolford, A. J.-A.; Woodhead, A. J.; Wyatt, P. G. U.S. Pat. Appl. Publ. 2008/0200509 A1, 2008.
40. Berdini, V.; O'Brien, M. A.; Carr, M. G.; Early, T. R.; Gill, A. L.; Trewartha, G.; Woolford, A. J.-A.; Woodhead, A. J.; Wyatt, P. G. U.S. Pat. Appl. Publ. 7825140 B2, 2010.
41. Gill, A. L.; Carr, M. G.; O'Brien, M. A.; Wyatt, P. G.; Berdini, V. U.S. Pat. Appl. Publ. 2008/0004270 A1, 2008.
42. For reviews on pyrazoles synthesis, see: Science of Synthesis; Stanovnik, B.; Svete, J. D., Eds.; Thieme: Stuttgart, 2002; Vol. 12, pp 22 - 81, 84 - 91.
43. Elguero, J. In Comprenhensive Heterocyclic Chemistry II; Shinkai, I., Ed.; Elsevier, Oxford, 1996; Vol. 3, pp 3 - 75. Recent examples, see
44. Okitsu, T.; Sato, K.; Wada, A. Org. Lett. 2010, 12, 3506
45. Goikhman, R.; Jacques, T. L.; Sames, D. J. Am. Chem. Soc. 2009, 131, 3042
46. For a recent report on Lewis acid-catalyzed the cleavage of C-S bond of dithioacetals, see: Tobisu, M.; Ito, S.; Kitajima, A.; Chatani, N. Org. Lett. 2008, 10, 5223