The study of Friedel-Crafts alkylation reaction of thiophenes with glyoxylate imine catalyzed by Fe(III): An easy access to α-aminoesters

Tetrahedron

Volumn 67, Issue 10, 2011, Pages 1788-1791

  Huang, Zhong ^a   Zhang, Jingchang ^a   Wang, Nai Xing ^b  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

^b TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Friedel Crafts reaction; Imine; Thiophenes; Aminoesters

Indexed keywords

ESTER DERIVATIVE; FERRIC CHLORIDE; GLYOXYLIC ACID DERIVATIVE; GLYOXYLIC ACID IMINE; IMINE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; REACTION OPTIMIZATION;

EID: 79951588913     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.01.039     Document Type: Article

References (51)

1. R.M. Roberts, and A.A. Khalaf Friedel-Crafts Alkylation Chemistry. A Century of Discovery 1984 Marcel Dekker New York, NY
2. M.B. Smith Organic Synthesis 1994 McGraw-Hill New York, NY p 1313
3. M. Bandini, A. Melloni, and A. Umani-Ronchi Angew. Chem., Int. Ed. 43 2004 550
4. M. Soueidan, J. Collin, and R. Gil Tetrahedron Lett. 47 2006 5467
5. J.-L. Zhao, L. Liu, H.-B. Zhang, Y.-C. Wu, D. Wang, and Y.-J. Chen Synlett 2006 96
6. T. Kano, A. Yamamoto, and K. Maruoka Tetrahedron Lett. 49 2008 5369
7. W. Wang, J. Wang, and H. Li Tetrahedron Lett. 45 2004 7243
8. A.J.A. Cobb, D.M. Shaw, D.A. Longbottom, J.B. Gold, and S.V. Ley Org. Biomol. Chem. 3 2005 84
9. A. Odedra, and P.H. Seeberger Angew. Chem., Int. Ed. 48 2009 2699
10. M. Mauksch, S.B. Tsogoeva, I.M. Martynova, and S. Wei Angew. Chem., Int. Ed. 46 2007 393
11. H. Zhang, Y. Chuan, Z. Li, and Y. Penga Adv. Synth. Catal. 351 2009 2288
12. H. Zhang, S. Mitsumori, N. Utsumi, M. Imai, N. Garcia-Delgado, M. Mifsud, K. Albertshofer, P.H.-Y. Cheong, K.N. Houk, F. Tanaka, and C.F. Barbas J. Am. Chem. Soc. 130 2008 875
13. H. Zhang, M. Mifsud, F. Tanaka, and C.F. Barbas J. Am. Chem. Soc. 128 2006 9630
14. S. Mitsumori, H. Zhang, P.H.-Y. Cheong, K.N. Houk, F. Tanaka, and C.F. Barbas J. Am. Chem. Soc. 128 2006 1040
15. E. Alza, C. Rodríguez-Escrich, S. Sayalero, A. Bastero, and M.A. Perics Chem.-Eur. J. 15 2009 10167
16. T. Kano, Y. Yamaguchi, and K. Maruoka Chem.-Eur. J. 15 2009 6678
17. N. Utsumi, H. Zhang, F. Tanaka, and C.F. Barbas Angew. Chem., Int. Ed. 46 2007 1878
18. K.R. Knudsen, and K.A. Jørgensen Org. Biomol. Chem. 3 2005 1362
19. S. Kobayashi, T. Gustafsson, Y. Shimizu, H. Kiyohara, and R. Matsubara Org. Lett. 8 2006 4923
20. M. Rueping, and A.P. Antonchick Org. Lett. 10 2008 1731
21. N. Nishiwaki, K.R. Knudsen, K.V. Gothelf, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 2992
22. S. Basra, M.W. Fennie, and M.C. Kozlowski Org. Lett. 8 2006 2659
23. R.D. McCullough Adv. Mater. 10 1998 93
24. M. Sebastian, M. Hissler, C. Fave, J. Rault-Berthelot, C. Odin, and R. Réau Angew. Chem., Int. Ed. 45 2006 6152
25. Z. Han, J. Zhang, X. Yang, H. Zhu, and W. Cao Sol. Energy Mater. Sol. Cells 94 2010 755
26. I.T. Hwang, H.R. Kim, D.J. Jeon, K.S. Hong, J.H. Song, and K.Y. Cho J. Agric. Food Chem. 53 2005 8639
27. N. Fokialakis, C.L. Cantrell, S.O. Duke, A.L. Skaltsounis, and D.E. Wedge J. Agric. Food Chem. 54 2006 1651
28. J.C. Sheehan, and K.R. Henery-Logan J. Am. Chem. Soc. 79 1957 1262
29. J.C. Sheehan, and K.R. Henery-Logan J. Am. Chem. Soc. 81 1959 3089
30. M. Friedman J. Agric. Food Chem. 52 2004 385
31. K. Turner Org. Process Res. Dev. 14 2010 311
32. N.A. Farid, R.L. Smith, T.A. Gillespie, T.J. Rash, P.E. Blair, A. Kurihara, and M.J. Goldberg Drug Metab. Dispos. 35 2007 1096
33. J.-M. Pereillo, M. Maftouh, A. Andrieu, M.-F. Uzabiaga, O. Fedeli, P. Savi, M. Pascal, J.-M. Herbert, J.-P. Maffrand, and C. Picard Drug Metab. Dispos. 30 2002 1288
34. D. Dalvie, P. Kang, M. Zientek, C. Xiang, S. Zhou, and R.S. Obach Chem. Res. Toxicol. 21 2008 2260
35. D. Dalvie, R.S. Obach, P. Kang, C. Prakash, C.-M. Loi, S. Hurst, A. Nedderman, L. Goulet, E. Smith, H.-Z. Bu, and D.A. Smith Chem. Res. Toxicol. 22 2009 357
36. G.G. Tu, S.H. Li, H.M. Huang, G. Li, F. Xiong, X. Mai, H.W. Zhu, B.H. Kuang, and W.F. Xu Bioorg. Med. Chem. 16 2008 6663
37. H. Vase, T.G. Lauridsen, J.N. Bech, and E.B. Pedersen Br. J. Clin. Pharmacol. 65 2008 822
38. S.F. Betz, Y.-F. Zhu, C. Chen, and R.S. Struthers J. Med. Chem. 51 2008 3331
39. S. Shirakawa, R. Berger, and J.L. Leighton J. Am. Chem. Soc. 127 2005 2858
40. T. Andreassen, L.-K. Hansen, and O.R. Gautun Eur. J. Org. Chem. 2008 4871
41. Y. Luo, and C.-J. Li Chem. Commun. 2004 1930
42. N. Sakai, J. Asano, Y. Shimano, and T. Konakahara Tetrahedron 64 2008 9208
43. S. Saaby, P. Bayon, P.S. Aburel, and K.A. Jørgensen J. Org. Chem. 67 2002 4352
44. J. Esquivias, R.G. Array, and J.C. Carretero Angew. Chem., Int. Ed. 45 2006 629
45. A. Kawada, S. Mitamura, and S. Kobayashi Chem. Commun. 1996 183
46. S. Kobayashi, and I. Komoto Tetrahedron 56 2000 6463
47. For the preparation of 1e-h, please see:
48. M. Rueping, B.J. Nachtsheim, and W. Ieawsuwan Adv. Synth. Catal. 348 2006 1033
49. I. Iovel, K. Mertins, J. Kischel, A. Zapf, and M. Beller Angew. Chem., Int. Ed. 44 2005 3913
50. H.-M. Dong, H.-H. Lu, L.-Q. Lu, C.-B. Chen, and W.-J. Xiao Adv. Synth. Catal. 349 2007 1597
51. Huang, Z.; Zhang, J. C.; Zhou, Y. Q.; Wang N.-X. Eur. J. Org. Chem. doi: 10.1002/ejoc.201001455.