A practical system to synthesize the multiple-substituted 2,5-dihydrofuran by the intermolecular dipolar cycloaddition reactions involving acceptor/acceptor-substituted diazo reagents

Tetrahedron

Volumn 67, Issue 30, 2011, Pages 5507-5515

  Zhu, Shifa ^a   Chen, Lijuan ^a   Wang, Chao ^a   Liang, Renxiao ^a   Wang, Xiujun ^a   Ren, Yanwei ^a   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

2,5 Dihydrofuran; Cycloaddition; Diazo; Dipolar; Heterocycle

Indexed keywords

1,3 DIOXOLANE; 2,5 DIHYDROFURAN DERIVATIVE; ALDEHYDE; AZO COMPOUND; DICARBOXYLIC ACID DERIVATIVE; FURAN DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 79959331072     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.028     Document Type: Article

References (45)

1. K.V. Gothelf, and K.A. Jørgensen Chem. Rev. 98 1998 863
2. A. Padwa, and S.F. Hornbuckle Chem. Rev. 91 1991 263
3. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds 1998 John Wiley New York, NY
4. J. Adams, and D.M. Spero Tetrahedron 47 1991 1765
5. G. Mehta, and S. Muthusamy Tetrahedron 58 2002 9477
6. A. Padwa, D.C. Dean, M.H. Osterhout, L. Precedo, and M.A. Semones J. Org. Chem. 59 1994 5347
7. S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, and S. Hashimoto J. Am. Chem. Soc. 121 1999 1417
8. A. Padwa, L. Precedo, and M.A. Semones J. Org. Chem. 64 1999 4079
9. M. Hamaguchi, H. Matsubara, and T. Nagai J. Org. Chem. 66 2001 5395
10. M. Muthusamy, C. Gunanthan, and E. Suresh Tetrahedron 60 2004 7885
11. S. Torssell, and P. Somfai Adv. Synth. Catal. 348 2006 2421
12. C.V. Galliford, and K.A. Scheidt J. Org. Chem. 72 2007 1811
13. J. Shi, M. Zhao, M. Lei, and M. Shi J. Org. Chem. 73 2008 305
14. D.B. England, J.M. Eagan, G. Merey, O. Anac, and A. Padwa Tetrahedron 64 2008 988
15. D.B. England, and A. Padwa J. Org. Chem. 73 2008 2792
16. P. de March, and R. Huisgen J. Am. Chem. Soc. 104 1982 4952
17. M.P. Doyle, D.C. Forbes, M.N. Protopopova, S.A. Stanley, M.M. Vasbinder, and K.R. Xavier J. Org. Chem. 62 1997 7210
18. A.E. Russell, J. Brekan, L. Gronenberg, and M.P. Doyle J. Org. Chem. 69 2004 5269
19. B. Jiang, X. Zhang, and Z. Luo Org. Lett. 4 2002 2453
20. M. Alt, and G. Mass Tetrahedron 50 1994 7435
21. E. Wenkert, and H. Khatuya Tetrahedron Lett. 40 1999 5439
22. A. DeAngelis, P. Panne, G.P.A. Yap, and J.M. Fox J. Org. Chem. 73 2008 1435
23. V. Nair, S. Mathai, S.M. Nair, and N.P. Rath Tetrahedron Lett. 44 2003 8407
24. V. Nair, S. Mathai, S.C. Mathew, and N.P. Rath Tetrahedron 61 2005 2849
25. C.-D. Lu, Z.-Y. Chen, H. Liu, W.-H. Hu, and A.-Q. Mi Org. Lett. 6 2004 3071
26. R. Huisgen, and P. de March J. Am. Chem. Soc. 104 1982 4953
27. M. Alt, and G. Maas Tetrahedron 50 1994 7435
28. M. Alt, and G. Maas Chem. Ber. 127 1994 1537
29. A. DeAngelis, M.T. Taylor, and J.M. Fox J. Am. Chem. Soc. 131 2009 1101
30. S.F. Zhu, J.A. Perman, and X.P. Zhang Angew. Chem., Int. Ed. 47 2008 8460
31. S.F. Zhu, X. Xu, J.A. Perman, and X.P. Zhang J. Am. Chem. Soc. 132 2010 12796
32. H. Heaney, and J.S. Ahn A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon Oxford 297 436
33. T. Eicher, and S. Hauptmann The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications 2003 Wiley-VCH Weinheim
34. B.H. Lipshutz Chem. Rev. 86 1986 795
35. J. Deli, P. Mólnar, G. Tóth, A. Baumeler, and C.H. Eugster Helv. Chim. Acta 74 1991 819
36. F. Perron, and K.F. Albizati Chem. Rev. 89 1989 1617
37. T.G. Kilroy, T.P. O'Sullivan, and P.J. Guiry Eur. J. Org. Chem. 2005 4929
38. A. Buzas, F. Istrate, and F. Gagosz Org. Lett. 8 2006 1957
39. Y. Liu, F. Song, Z. Song, M. Liu, and B. Yan Org. Lett. 7 2005 5409
40. S. Ma, and W. Gao J. Org. Chem. 67 2002 6104
41. Y. Deng, Y. Shi, and S. Ma Org. Lett. 11 2009 1205
42. V. Thottempudi, H. Gao, and J.M. Shreeve J. Am. Chem. Soc. 133 2011 6464
43. R. Shelkov, M. Nahmany, and A. Melman J. Org. Chem. 67 2002 8975
44. Y. Liu, and L. Zhang Tetrahedron 64 2008 10728
45. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian Pittsburgh, PA