Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes

Tetrahedron Letters

Volumn 50, Issue 23, 2009, Pages 2740-2743

  Kanomata, Nobuhiro ^a   Suzuki, Jun ^b   Kubota, Hironobu ^b   Nishimura, Kiichiro ^a   Enomoto, Terumichi ^b  

^a WASEDA UNIVERSITY   (Japan)

^b MEIJI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; BIPYRIDINE; METAL; NICOTINIC ACID; PYRIDINE DERIVATIVE; PYRIDINOPHANE; TERPYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CROSS COUPLING REACTION; NEGISHI REACTION; STILLE REACTION; SYNTHESIS;

EID: 64549111258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.095     Document Type: Article

References (43)

1. For recent review articles regarding bipyridines and terpyridines, see:. Hapke M., Brandtb L., and Lützen A. Chem. Soc. Rev. 37 (2008) 2782-2797
2. Kwong H.-L., Yeung H.-L., Yeung C.-T., Lee W.-S., Lee C.-S., and Wong W.-L. Coord. Chem. Rev. 251 (2007) 2188-2222
3. Chelucci G., and Thummel R.P. Chem. Rev. 102 (2002) 3129-3170
4. Hrdina R., Dracinsky M., Valterova I., Hodacova J., Cisarova I., and Kotora M. Adv. Synth. Catal. 350 (2008) 1449-1456
5. Goswami A., Ohtaki K., Kase K., Ito T., and Okamoto S. Adv. Synth. Catal. 350 (2008) 143-152
6. Lawecka J., Bujnicki B., Drabowicz J., and Rykowski A. Tetrahedron Lett. 49 (2008) 719-722
7. Ricardo C., and Pintauer T. J. Org. Chem. 692 (2007) 5165-5172
8. For references of asymmetric reactions with bipyridines:. Malkov A.V., Bell M., Orsini M., Pernazza D., Massa A., Herrmann P., Meghani P., and Kočovsky P. J. Org. Chem. 68 (2003) 9659-9668
9. Lyle M.P.L., and Wilson P.D. Org. Lett. 6 (2004) 855-857
10. Yeung C.-T., Teng P.-F., Yeung H.-L., Wong W.-T., and Kwong H.-L. Org. Biomol. Chem. 5 (2007) 3859-3864
11. Chen Y.-J., Lin R.-X., and Chen C. Tetrahedron: Asymmetry 15 (2004) 3561-3571
12. For recent articles covering terpyridines, see: Refs. 1b,c,2b,3b,c and references cited therein.
13. For asymmetric reactions with terpyridine ligands:. Wong W.-L., Lee C.-S., Leung H.-K., and Kwong H.-L. Org. Biomol. Chem. 2 (2004) 1967-1969
14. Wong W.-L., Lee W.-S., and Kwong H.-L. Tetrahedron: Asymmetry 13 (2002) 1485-1492
15. Kwong H.-L., Wong W.-L., Lee W.-S., Cheng L.-S., and Wong W.-T. Tetrahedron: Asymmetry 12 (2001) 2683-2694
16. Kwong H.-L., and Lee W.-S. Tetrahedron: Asymmetry 11 (2000) 2299-2308
17. Chelucci G., Saba A., Soccolini F., and Vignola D. J. Mol. Catal. A: Chem. 178 (2002) 27-33
18. Chelucci G., Saba A., Vignola D., and Solinas C. Tetrahedron 57 (2001) 1099-1104
19. Wörsdörfer U., Vögtle F., Nieger M., Waletzke M., Grimme S., Glorius F., and Pfaltz A. Synthesis (1999) 597-602
20. Wörsdörfer U., and Vögtle F. J. Prakt. Chem. (1999) 445-448
21. Rios R., Liang G., Lo M.M.-C., and Fu G.C. J. Chem. Soc., Chem. Commun. (2000) 377-378
22. Kanomata N., and Nakata T. J. Am. Chem. Soc. 122 (2000) 4563-4568
23. Kanomata N., and Nakata T. Angew. Chem., Int. Ed. Engl. 36 (1997) 1207-1211
24. Kanomata N., Yamada S., Ohhama T., Fusano A., Ochiai Y., Oikawa J., Yamaguchi M., and Sudo F. Tetrahedron 62 (2006) 4128-4138
25. Ueda T., Kanomata N., and Machida H. Org. Lett. 7 (2005) 2365-2368
26. Kanomata N., and Ochiai Y. Tetrahedron Lett. 42 (2001) 1045-1048
27. Kanomata N., Maruyama S., Tomono K., and Anada S. Tetrahedron Lett. 44 (2003) 3599-3603
28. Kanomata N., Mishima G., and Onozato J. Tetrahedron Lett. 50 (2009) 409-412
29. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176-4211
30. Jung J.-C., Jung Y.-J., and Park O.-S. Synth. Commun. 31 (2001) 2507-2511
31. The corresponding carboxylic acid resulted from hydrolysis with TMSI in ca. 40% ratio.
32. Schlosser M., and Cottet F. Eur. J. Org. Chem. (2002) 4181-4184
33. Mee S.P.H., Lee V., and Baldwin J.E. Angew. Chem., Int. Ed. 43 (2004) 1132-1136
34. +] 353.2229, found 353.2228.
35. Tiecco M., Testaferri L., Tingoli M., Chianelli D., and Montanucci M. Synthesis (1984) 736-738
36. Ling R., Yoshida M., and Mariano P.S. J. Org. Chem. 61 (1996) 4439-4449
37. +] 549.3692, found 549.3661.
38. 3) δ 0.38 (s, 9H), 7.27-7.29 (m, 1H), 7.44-7.46 (m, 1H), 7.66 (t, J = 7.6 Hz, 1H), 7.79-7.81 (m, 1H), 8.25-8.27 (m, 1H), 8.54 (d, J = 8.0 Hz, 1H), 8.66 (m, 1H).
39. +] 386.2591, found 386.2598.
40. Yamamoto Y., and Yanagi A. Chem. Pharm. Bull. Jpn. 30 (1982) 1731-1737
41. +] 538.4161, found 538.4161.
42. 2 are 0.0358 and 0.0675, respectively [I > 2.00s(I)]. Crystallographic data (excluding structure factors) for the structure of (S, S)-7 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication No. CCDC 722776. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
43. 4Zn: C, 59.61; H, 7.06; N, 4.09. found: C, 58.22; H, 7.18; N, 3.91.