An efficient Morita-Baylis-Hillman reaction for the synthesis of multifunctional 2-hydroxy-3-nitrobut-3-enoate derivatives

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9875-9879

  Kuan, Hsuan Hao ^a   Reddy, Raju Jannapu ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

Aqueous media; Morita Baylis Hillman reaction; Nitroalkenes; Organocatalysis; Thiourea

Indexed keywords

2 HYDROXY 3 NITROBUT 3 ENOATE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; HYDROXYL GROUP; IMIDAZOLE; NITROALKANE; SOLVENT; THIOUREA; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MORITA BAYLIS HILLMAN REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 78649651275     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.061     Document Type: Article

References (55)

1. Hillman, M. E. D.; Baylis, A. B. U.S. Patent US 3,743,669, 1973;
2. Morita, A. B.; Hillman, M. E. D. Ger. Offen. DE 2155113, 1972;
3. Chem. Abstr. 77 1972 434174
4. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jpn. 41 1968 2815
5. H. Kurasaki, I. Okamoto, N. Morita, and O. Tamura Org. Lett. 11 2009 1179
6. Y.-L. Shi, Y.-M. Xu, and M. Shi Adv. Synth. Catal. 346 2004 1220
7. A. Bugarin, and B.T. Connell J. Org. Chem. 74 2009 4638
8. M. Shi, and X.-G. Liu Org. Lett. 10 2008 1043
9. L. He, T.-Y. Jian, and S. Ye J. Org. Chem. 72 2007 7466
10. C.E. Aroyan, M.M. Vasbinder, and S.J. Miller Org. Lett. 7 2005 3849
11. M.E. Krafft, and T.F.N. Haxell J. Am. Chem. Soc. 127 2005 10168
12. S. Luo, B. Zhang, J. He, A. Janczuk, P.G. Wang, and J.-P. Cheng Tetrahedron Lett. 43 2002 7369
13. R. Gatri, and M.M.E. Gaïed Tetrahedron Lett. 43 2002 7835
14. D. Basavaiah, M. Krishnamacharyulu, and A.J. Rao Synth. Commun. 30 2000 2061
15. S. Rafel, and J.W. Leahy J. Org. Chem. 62 1997 1521
16. Z. Wu, G. Zhou, J. Zhou, and W. Guo Synth. Commun. 36 2006 2491
17. C. Yu, and L. Hu J. Org. Chem. 67 2002 219
18. For recent reviews on MBH reactions see:
19. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1
20. V. Singh, and S. Batra Tetrahedron 64 2008 4511
21. Y.-L. Shi, and M. Shi Eur. J. Org. Chem. 2007 2905
22. D. Basavaiah, K.V. Rao, and R.J. Reddy Chem. Soc. Rev. 36 2007 1581
23. T. Kataoka, and H. Kinoshita Eur. J. Org. Chem. 2005 45
24. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811
25. D. Basavaiah, P.D. Rao, and R.S. Hyma Tetrahedron 52 1996 8001
26. S.E. Drewes, and G.H.P. Roos Tetrahedron 44 1988 4653
27. J. Mack, and M. Shumba Green Chem. 9 2007 328
28. V.K. Aggarwal, D.K. Dean, A. Mereu, and R. Williams J. Org. Chem. 67 2002 510
29. W.D. Lee, K.S. Yang, and K. Chen Chem. Commun. 2001 1612
30. J.-J. Gong, K. Yuan, and X.-Y. Wu Tetrahedron: Asymmetry 20 2009 2117
31. K. Yuan, L. Zhang, H.-L. Song, Y. Hu, and X.-Y. Wu Tetrahedron Lett. 49 2008 6262
32. J. Vesely, R. Rios, and A. Córdova Tetrahedron Lett. 49 2008 1137
33. V.Y. Korotaev, V.Y. Sosnovskikh, I.B. Kutyashev, A.Y. Barkov, E.G. Matochkina, and M.I. Kodess Tetrahedron 64 2008 5055
34. M. Dadwal, S.M. Mobin, and I.N.N. Namboothiri Org. Biomol. Chem. 4 2006 2525
35. M. Dadwal, R. Mohan, D. Panda, S.M. Mobin, and I.N.N. Namboothiri Chem. Commun. 2006 338
36. N. Rastogi, I.N.N. Namboothiri, and M. Cojocaru Tetrahedron Lett. 45 2004 4745
37. Y.-L. Shi, and M. Shi Org. Biomol. Chem. 5 2007 1499
38. G.-N. Ma, S.-H. Cao, and M. Shi Tetrahedron: Asymmetry 20 2009 1086
39. R. Mohan, N. Rastogi, I.N.N. Namboothiri, S.M. Mobin, and D. Panda Bioorg. Med. Chem. 14 2006 8073
40. N. Rastogi, R. Mohan, D. Panda, S.M. Mobin, and I.N.N. Namboothiri Org. Biomol. Chem. 4 2006 3211
41. K.-Y. Zee-Cheng, and C.-C. Cheng J. Med. Chem. 12 1969 157
42. J. Paradowska, M. Stodulski, and J. Mlynarski Angew. Chem., Int. Ed. 48 2009 4288
43. R.O.M.A. Souza, V.L.P. Pereira, P.M. Esteves, and M.L.A.A. Vasconcellos Tetrahedron Lett. 49 2008 5902
44. I. Deb, P. Shanbhag, S.M. Mobin, and I.N.N. Namboothiri Eur. J. Org. Chem. 2009 4091
45. I. Deb, M. Dadwal, S.M. Mobin, and I.N.N. Namboothiri Org. Lett. 8 2006 1201
46. C. Chang, S.-H. Li, R.J. Reddy, and K. Chen Adv. Synth. Catal. 351 2009 1273
47. R.J. Reddy, H.-H. Kuan, T.-Y. Chou, and K. Chen Chem. - Eur. J. 15 2009 9294
48. P.-M. Liu, C. Chang, R.J. Reddy, Y.-F. Ting, H.-H. Kuan, and K. Chen Eur. J. Org. Chem. 2010 42
49. D.R. Magar, C. Chang, Y.-F. Ting, and K. Chen Eur. J. Org. Chem. 2010 2062
50. Y.-F. Ting, C. Chang, R.J. Reddy, D.R. Magar, and K. Chen Chem. - Eur. J. 16 2010 7030
51. P.-M. Liu, D.R. Magar, and K. Chen Eur. J. Org. Chem. 2010 5705
52. Y. Sohtome, N. Takemura, R. Takagi, Y. Hashimoto, and K. Nagasawa Tetrahedron 64 2008 9423
53. D.J. Maher, and S.J. Connon Tetrahedron Lett. 45 2004 1301
54. The reaction of nitroalkenes with some activated carbonyl compounds, such as pyruvate, phenyl glyoxylate, and diethyl ketomalonate was studied. Unfortunately, the reactions proceeded to give either low chemical yields or led to complex products under the optimum reaction conditions.
55. Detailed X-ray crystallographic data is available from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK for product 3a (CCDC No. 795732).