Regioselectivity of Diels-Alder reactions between 6,7-dehydrobenzofuran and 2-substituted furans

Tetrahedron Letters

Volumn 53, Issue 31, 2012, Pages 4022-4025

  Brown, Neil ^a   Buszek, Keith R ^b  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

Arynes; Benzofurans; Benzofuranyne; Cycloaddition; Dehydrobenzofuran; Diels Alder; Furans; Indole; Indolyne; Regioselective

Indexed keywords

2 FURANONE DERIVATIVE; 6,7 DEHYDROBENZOFURAN; FURAN DERIVATIVE; HALOGEN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLOADDITION; DIELS ALDER REACTION; ELIMINATION REACTION; HALOGENATION; METAL BINDING;

ALNUS;

EID: 84862645403     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.118     Document Type: Article

References (31)

1. J.D. Roberts, H.E. Simmons Jr., L.A. Carlsmith, and C.W. Vaughan J. Am. Chem. Soc. 75 1953 3290 3291
2. J.D. Roberts, D.A. Semenow, H.E. Simmons Jr., and L.A. Carlsmith J. Am. Chem. Soc. 78 1956 601 611
3. For a review of arynes, see: C.M. Gampe, and E.M. Carreira Angew. Chem., Int. Ed. 51 2012 3766 3778
4. R.W. Hoffmann Dehydrobenzene and Cycloalkynes 1967 Academic New York
5. H. Pellissier, and M. Santelli Tetrahedron 59 2003 701 730
6. H.H. Wenk, M. Winkler, and W. Sander Angew. Chem., Int. Ed. 42 2003 502 528
7. M.G. Reinecke Tetrahedron 38 1982 427 498
8. Pyridynes: T. Kauffmann, and F.P. Boettcher Angew. Chem. 73 1961 65 66
9. R.J. Martens, and H.J. den Hertog Tetrahedron Lett. 1962 643 645
10. Naphthalynes: J.F. Bunnett, and T.K. Brotherton J. Org. Chem. 23 1958 904 906
11. R. Huisgen, and L. Zirngibl Chem. Ber. 91 1958 1438 1452
12. K.R. Buszek, D. Luo, M. Kondrashov, N. Brown, and D. VanderVelde Org. Lett. 9 2007 4135 4137
13. K.R. Buszek, N. Brown, and D. Luo Org. Lett. 11 2009 201 204
14. N. Brown, D. Luo, D. VanderVelde, S. Yang, A. Brassfield, and K.R. Buszek Tetrahedron Lett. 50 2009 63 65
15. N. Brown, D. Luo, J.A. Decapo, and K.R. Buszek Tetrahedron Lett. 50 2009 7113 7115
16. A.N. Garr, D. Luo, N. Brown, C.J. Cramer, K.R. Buszek, and D. VanderVelde Org. Lett. 12 2010 96 99
17. P.D. Thornton, N. Brown, D. Hill, B. Neuenswander, G.H. Lushington, C. Santini, and K.R. Buszek ACS Comb. Sci. 13 2011 443 448
18. S.M. Bronner, K.B. Bahnck, and N.K. Garg Org. Lett. 11 2009 1007 1010
19. X. Tian, A.D. Huters, C.J. Douglas, and N.K. Garg Org. Lett. 11 2009 2349 2351
20. P.H.-Y. Cheong, R.S. Paton, S.M. Bronner, G.-Y.J. Im, N.K. Garg, and K.N. Houk J. Am. Chem. Soc. 132 2010 1267 1269
21. G.-Y.J. Im, S.M. Bronner, A.E. Goetz, R.S. Paton, P.H.-Y. Cheong, K.N. Houk, and N.K. Garg J. Am. Chem. Soc. 132 2010 17933 17944
22. S.M. Bronner, A.E. Goetz, and N.K. Garg J. Am. Chem. Soc. 133 2011 3832 3835
23. A.E. Goetz, S.M. Bronner, J.D. Cisneros, J.M. Melamed, R.S. Paton, K.N. Houk, and N.K. Garg Angew. Chem. 124 2012 2812 2816
24. For a recent review see: A.J. Kochanowska-Karamyan, and M.T. Hamann Chem. Rev. 110 2010 4489 4497
25. G.D. McCallion Curr. Org. Chem. 1999 67 76
26. S.M. Hoy, and S.J. Keam Drugs 69 2009 1647 1663
27. L. Wei, L. Jianchang, D. DeVincentis, and T.S. Mansour Tetrahedron 64 2008 7871 7876
28. P. Barker, P. Finke, and K. Thompson Synth. Commun. 19 1989 257 265
29. C. Dallaire, I. Kolber, and M. Gingras Org. Synth. 78 2002 42 50
30. For a review of DoM see: V. Snieckus Chem. Rev. 90 1990 879 933
31. M. Dixit, A. Sharon, P.R. Maulik, and A. Goel Synlett 2006 1497 1502