Use of the Diels-Alder cycloaddition of tetracyclone and internal aryl acetylenes for the synthesis of functionalized atropisomeric biaryls

European Journal of Organic Chemistry

Volumn , Issue 3, 2010, Pages 509-514

  Hapke, Marko ^a   Gutnov, Andrey ^a   Weding, Nico ^a   Spannenberg, Anke ^a   Fischer, Christine ^a   Benkhäuser Schunk, Christian ^b   Heller, Barbara ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Alkynes; Atropisomerism; Biaryls; Cycloaddition; Diels alder reaction

Indexed keywords

EID: 74549186436     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901080     Document Type: Article

References (39)

1. Examples: a) C. J. Walsh, B. K. Mandai, J. Org. Chem. 1999, 64, 6102-6105;
2. b) P. J. Steel, N. C. Webb, Eur. J. Inorg. Chem. 2002, 2257-2260;
3. c) L. Cracium, D. M. Ho, M. Jones Jr., R. A. Pascal Jr., Tetrahedron Lett. 2004, 45, 4985-4987;
4. d) R. G. Potter, T. S. Hughes, Org. Lett. 2007, 9, 1187-1190.
5. Recent reviews on the synthesis of dendrimers by cycloaddition. reactions: a) B. Voit, New J. Chem. 2007, 31, 1139-1151;
6. b) G. Franc, A. K. Kakkar, Chem. Eur. J. 2009, 15, 5630-5639.
7. a) R. Rathore, C. L. Bums, S. A. Abdelwahed, Org. Lett. 2004, 6, 1689-1692;
8. b) H. Komber, K. Stumpe, B. Voit, Tetrahedron Lett. 2007, 48, 2655-2659.
9. Examples: a) V. S. Iyer, M. Wehmeier, J. D. Brand, M. A. Keegstra, K. Müllen, Angew. Chem. Int. Ed. Engl. 1997, 36, 1604-1607;
10. b) M. Müller, V. S. Iyer, C. Kübel, V. Enkelmann, K. Müllen, Angew. Chem. Int. Ed. Engl. 1.997, 36, 1607-1610;
11. c) C. J. Walsh, B. K. Mandal, J. Org. Chem. 1999, 64, 6102-6105;
12. d) F. Dötz, J. D. Brand, S. Ito, L. Gherghel, K. Müllen, J. Am. Chem. Soc, 2000, 122, 7707-7717;
13. e) S. M. Draper, D. J. Gregg, R. Madathil, J. Am. Chem. Soc, 2002, 124, 3486-3487;
14. f) A. H. M. Elwahy, Tetrahedron Lett. 2002, 43, 711-714;
15. g) S. Ito, A. Nomura, N. Morita, C. Kabuto, H. Kobayashi, S. Maejima, K. Fujimoro, M. Yasunami, J. Org. Chem. 2002, 67, 7295-7302;
16. h) J. Wu, A. Fechtenkötter, J. Gauss, M. D. Watson, M. Kastler, C. Fechtenkötter, M. Wagner, K. Müllen, J. Am. Chem. Soc, 2004, 126, 11311-11321;
17. i) K. E. MaIy, E. Gagnon, T. Maris, J. D. Wuest, J. Am. Chem. Soc. 2007, 129, 4306-4322.
18. S. Ito, M. Wehmeier, J. D. Brand, C Kübel, R. Epsch, J. P. Rabe, K. Müllen, Chem. Eur. J. 2000, 6, 4327-4342.
19. Recent examples: a) C. M. A. Ollagnier, S. D. Perera, C. M. Fitchett, S. M. Draper, Dalton Trans. 2008, 283-290;
20. b) P. Du, J. Schneider, W. W. Brennessel, R. Eisenberg, Inorg. Chem. 2008, 47, 69-77;
21. c) M. C. Haberecht, J. M. Schnorr, E. V. Andreitchenko, C. G. Clark Jr., M. Wagner, K. Müllen, Angew. Chem, Int. Ed. 2008, 47, 1662-1667.
22. C. F. H. Allen, Chem. Rev. 1962, 62, 653-664.
23. a) D. Gust, J. Am. Chem. Soc. 1977, 99, 6980-6982;
24. b) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
25. T. Iwasawa, T. Komano, A. Tajima, M. Tokunaga, Y. Obora, T. Fujihara, Y. Tsuji, Organometallics 2006, 25, 4665-4669.
26. Examples: a) B. O. Ashburn, R. G. Carter, Angew. Chem. Int. Ed. 2006, 45, 6737-674.1;
27. b) S. Doherty, CH. Smyth, R. W Harrington, W. Clegg, Organometallics 2009, 28, 5273-5276, and references cited therein.
28. a) A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spaniienberg, C. Sundermann, B. Sundermann, Angew. Chem. Int. Ed. 2004, 43, 379-3797;
29. b) B. Heller, A. Gutnov, C. Fischer, H.-J. Drexler, A. Spannenberg, D. Redkin, C. Sundermann, B. Sun-dermann, Chem. Eur. J. 2007, 13, 1117-1128;
30. c) B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085-1094.
31. CCDC-733394 contains the supplementary crystallograpliic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
32. 2 in. reductions: a) M. S. Morales-Ríos, O. R. Suárez-Castillo, J. J. Trujillo-Serrato, P. Joseph-Nathan, J. Org. Chem. 2001, 66, 1186-1192;
33. b) T. Kawasaki, M. Shinada, M. Ohzono, A. Ogawa, R. Terashima, M. Sakamoto, J. Org. Chem. 2008, 73, 5959-5964. The use of these aluminium-based reagents therefore seemed to be problematic in some cases with highly substituted biaryl phosphane oxides.
34. a) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945-1948;
35. b) Y. Uozumi, N. Suzuki, A. Ogi- wara, T. Hayashi, Tetrahedron 1994, 50, 4293-4302;
36. c) J.-M. VaIk, T. D. W Claridge, J. M. Brown, D. Hibbs, M. B. Hursthouse, Tetrahedron: Asymmetry 1995, 6, 2597-2610;
37. d) Y. Uozumi, M. Kawatsura, T. Hayashi, Org. Synth. 2002, 78, 1-13;
38. e) A. Börner (Ed.), Phosphorus Ligands in Asymmetric Catalysis, Wiley-VCH, Weinheim, 2008.
39. A. Kondoh, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2007, 129, 6996-6997.