Synthesis of C2-Symmetric 2,2′-Bipyridines Derived from 4-Substituted 1,10,10-Trimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decane

Synthetic Communications

Volumn 34, Issue 7, 2004, Pages 1191-1197

  Davies, Stephen R ^a   Cain, Christopher P ^a   Glossop, Matthew T ^a   Mengent, Marie Laure ^a   Kee, Terence P ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

2,2 Bipyridines; Asymmetric synthesis; C2 Symmetry; R Configuration; S Configuration

Indexed keywords

1,10,10 TRIMETHYL 3 OXA 5 AZA TRICYCLO[5.2.1.0 2,6]DECANE; 2,2' BIPYRIDINE; 2,2' BIPYRIDINYL 6,6' DICARBOXALDEHYDE; 3 BUTYLAMINO 1,7,7 TRIMETHYL BICYCLO[2.2.1]HEPTAN 2 OL; 5 BUTYL 4 (6 BROMOPYRIDIN 2 YL) 1,10,10 TRIMETHYL 3 OXA 5 AZA TRICYCLO[5.2.1.0 2,6]DECANE; ADAMANTANE; ALDEHYDE; BIS 6,6' (5 BUTYL 1,10,10 TRIMETHYL 3 OXA 5 AZA TRICYCLO[5.2.1.0 2,6]DEC 4 YL) 2,2 BIPYRIDINE; HEPTANOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; POLYMERIZATION;

EID: 1842533477     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120030305     Document Type: Article

References (31)

1. (a) Bhasikuttan, A.C.; Suzuki, M.; Nakashima, S.; Okada, T. J. Am. Chem. Soc. 2002, 124, 8398;
2. (b) Osowole, A.A.; Woods, J.A.O.; Odunola, O.A. Synth. React. Metal-Org. Chem. 2002, 32, 783;
3. (c) Gong, X.; Ng, P.K.; Chan, W.K. J. Nanosci. Nanotech. 2002, 2, 151;
4. (d) Gelman, D.; Dechert, S.; Schumann, H.; Blum, J. Inorg. Chim. Acta 2002, 334, 149;
5. (e) Kinnunen, T.J.J.; Haukka, M.; Pakkanen, T.A. J. Organomet. Chem. 2002, 654, 8;
6. (f) Kuhn, F.E.; Groake, M.; Bencze, E.; Herdtweck, E.; Prazerer, A.; Santos, A.M.; Calhorda, M.J.; Romao, C.C.; Goncalves, I.S.; Lopes, A.D.; Pillinger, M. Chemistry - Eur. J. 2002, 8, 2370;
7. (g) Armaroli, N.; Accorsi, G.; Felder, D.; Nierengarten, J.-F. Chemistry-Eur. J. 2002, 8, 2323.
8. (a) Uenishi, J.; Hiraoka, T.; Hata, S.; Nishimaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481;
9. (b) Peterson, M.A.; Dalley, N.K. Synth. Commun. 1996, 26, 2223;
10. (c) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905;
11. (d) Fung, W.H.; Cheng, W.C.; Yu, W.Y.; Che, C.M.; Mak, T.C.W. J. Chem. Soc., Chem. Commun. 1995, 2007;
12. (e) Chelucci, G. Tetrahedron: Asymmetr. 1995, 6, 811;
13. (f) Nishiyama, H.; Yamaguchi, S.; Park S.B.; Itoh, K. Tetrahedron: Asymmetr. 1993, 4, 143;
14. (g) Chelucci, G. Gazz. Chim. Ital. 1992, 122, 89;
15. (h) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205;
16. (i) Cheluchi, G.; Falorni, M.; Giacomelli, G. Tetrahedron 1992, 48, 453;
17. (j) Hopkins, R.B.; Hamilton, A.D. J. Chem. Soc., Chem. Commun. 1987, 3, 171.
18. (a) Chittenden, R.A.; Cooper, G.H. J. Chem. Soc. C 1970, 49;
19. (b) Beckett, A.H.; Lan, N.T.; McDonough, G.R. Tetrahedron 1969, 25, 5689, 5693.
20. (a) Denmark, S.E.; Rivera, I. J. Org. Chem. 1994, 59, 6887;
21. (b) Feringa, B.L.; Jansen, J.F.G.A.; de Vries, A.H.M. Tetrahedron 1994, 50, 4479;
22. (c) Tanaka, K.; Ushio, H.; Kawabata, Y.; Susuki, H. J. Chem. Soc., Perkin Trans. 1 1991, 1445;
23. (d) Saigo, K.; Yamamoto, M.; Morimura, K.; Nohira, H. Chem. Lett. 1979, 8, 545;
24. (e) Forster M.O.; Thornley, T. J. Chem. Soc. 1909, 95, 942.
25. (a) Falk, H.; Suste, A. Monatsh 1993, 124, 881;
26. (b) Parks, J.E.; Holm, R.H. J. Organomet. Chem. 1973, 56, 53.
27. Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Japan 1990, 63, 80.
28. (a) Cabri, W.; Candiani, L. Acc. Chem. Res. 1995, 28, 2;
29. (b) Meije, A.J.; Meyer, F.F. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379;
30. (c) Stille, J.K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
31. Davies, S.R.; Mitchell, M.C.; Cain, C.P.; Devitt, P.G.; Taylor, R.J.; Kee, T.P. J. Organomet. Chem. 1998, 550, 29.